As filed with the Securities
and Exchange Commission on September 3, 2003.         Registration No. 333-
================================================================================

                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549
                                    FORM S-3
                             REGISTRATION STATEMENT
                        UNDER THE SECURITIES ACT OF 1933

                         WINTRUST FINANCIAL CORPORATION
             (Exact Name of Registrant as Specified in its Charter)


                                                                                      
              ILLINOIS                                727 NORTH BANK LANE                          36-3873352
    (State or Other Jurisdiction                LAKE FOREST, ILLINOIS 60045-1951                  (IRS Employer
 of Incorporation or Organization)                       (847) 615-4096                      Identification Number)
                                      (Address, Including Zip Code, and Telephone Number,
                                         Including Area Code, of Registrant's Principal
                                                       Executive Offices)


                                DAVID A. DYKSTRA
           SENIOR EXECUTIVE VICE PRESIDENT AND CHIEF OPERATING OFFICER
                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096

            (Name, Address, Including Zip Code, and Telephone Number,
                   Including Area Code, of Agent for Service)

      The Commission is requested to send copies of all communications to:

            JENNIFER R. EVANS, ESQ.                    TIMOTHY J. MELTON, ESQ.
          JENNIFER DURHAM KING, ESQ.                   EDWARD B. WINSLOW, ESQ.
    VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.                   JONES DAY
           222 NORTH LASALLE STREET                     77 WEST WACKER DRIVE
         CHICAGO, ILLINOIS 60601-1003                  CHICAGO, ILLINOIS 60601
                (312) 609-7500                             (312) 782-3939

         Approximate date of commencement of proposed sale to the public: As
soon as practicable after the effectiveness of this Registration Statement.

         If the only securities being registered on this Form are being offered
pursuant to dividend or interest reinvestment plans, check the following
box. [ ]

         If any of the securities being registered on this Form are to be
offered on a delayed or continuous basis pursuant to Rule 415 under the
Securities Act of 1933, other than securities offered only in connection with
dividend or interest reinvestment plans, check the following box. [ ]

         If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, check the following box and
list the Securities Act registration statement number of the earlier effective
registration statement for the same offering. [ ]

         If this Form is a post-effective amendment filed pursuant to Rule
462(c) under the Securities Act, check the following box and list the Securities
Act registration statement number of the earlier effective registration
statement for the same offering. [ ]

         If delivery of the prospectus is expected to be made pursuant to Rule
434, please check the following box. [ ]

                                 ---------------
                         CALCULATION OF REGISTRATION FEE


                                                                           
==================================== ================ ============================= =========================== =================
                                                                                         Proposed Maximum
      Title of Each Class of          Amount to be     Proposed Maximum Offering        Aggregate Offering         Amount of
    Securities to be Registered       Registered(1)      Price Per Share(1)                  Price(1)           Registration Fee
------------------------------------ ---------------- ----------------------------- --------------------------- -----------------
Common Stock, without par value*        1,150,000               $35.35                      $40,652,500              $3,293
==================================== ================ ============================= =========================== =================


*        Including the preferred share purchase rights associated therewith.
(1)      Estimated solely for the purpose of determining the registration fee
         pursuant to Rule 457(c), based on the average of the high and low sale
         prices on August 29, 2003, as reported on the Nasdaq National Market,
         of $35.50 and $35.20, respectively. --------------- THE REGISTRANT
         HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR DATES AS MAY
         BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL
         FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS
         REGISTRATION STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE
         WITH SECTION 8(a) OF THE SECURITIES ACT OF 1933, AS AMENDED, OR UNTIL
         THE REGISTRATION STATEMENT SHALL BECOME EFFECTIVE ON SUCH DATE AS THE
         COMMISSION, ACTING PURSUANT TO SAID SECTION 8(a), MAY DETERMINE.



The information in this prospectus is not complete and may be changed. We cannot
sell these securities until the Securities and Exchange Commission declares our
registration statement effective. This prospectus is not an offer to sell these
securities and it is not soliciting an offer to buy these securities in any
state where the offer or sale is not permitted.

                 Subject to completion, dated September 3, 2003.

PROSPECTUS
----------

                                1,000,000 SHARES

                         WINTRUST FINANCIAL CORPORATION
                                  COMMON STOCK
                             -----------------------

Wintrust Financial Corporation is offering 1,000,000 shares of its common stock.

Our common stock is traded on the Nasdaq National Market under the symbol
"WTFC." The last reported sale price of our common stock as reported on Nasdaq
on September 2, 2003 was $35.72 per share.

INVESTING IN OUR COMMON STOCK INVOLVES RISKS THAT ARE DESCRIBED IN THE "RISK
FACTORS" SECTION BEGINNING ON PAGE 13.

                            ------------------------
                                PRICE $ PER SHARE
                            ------------------------


                                                   PER SHARE    TOTAL
        Public offering price....................  $            $
        Underwriting discount....................  $            $
        Proceeds, before expenses, to Wintrust...  $            $

The underwriters may also purchase up to an additional 150,000 shares of common
stock from us at the public offering price, less the underwriting discount,
within 30 days from the date of this prospectus to cover over-allotments, if
any.

NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
COMMISSION HAS APPROVED OR DISAPPROVED OF THESE SECURITIES OR DETERMINED IF THIS
PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.

THESE SECURITIES ARE NOT SAVINGS ACCOUNTS, DEPOSITS OR OTHER OBLIGATIONS
OF ANY BANK AND ARE NOT INSURED OR GUARANTEED BY THE FEDERAL DEPOSIT INSURANCE
CORPORATION OR ANY OTHER GOVERNMENTAL AGENCY.

The shares of common stock will be ready for delivery on or about        , 2003.

                             -----------------------
RBC CAPITAL MARKETS
          U.S. BANCORP PIPER JAFFRAY
                              RAYMOND JAMES
                                     STIFEL, NICOLAUS & COMPANY
                                            INCORPORATED
                                                SANDLER O'NEILL & PARTNERS, L.P.

                             -----------------------
                                     , 2003



                      [MAP SHOWING LOCATIONS OF CURRENT AND
                    PENDING BANKING AND SUBSIDIARY OFFICES]



                                TABLE OF CONTENTS
                                                                         PAGE

Prospectus Summary..........................................................1
Summary Consolidated Financial Data.........................................9
Risk Factors...............................................................13
Use of Proceeds............................................................18
Capitalization.............................................................19
Price Range of Common Stock and Dividend Policy............................20
Underwriting...............................................................21
Transfer Agent.............................................................23
Legal Matters..............................................................23
Experts  ..................................................................23
Where You Can Find More Information........................................23
Documents Incorporated by Reference........................................23


                            ------------------------

         You should rely only on the information provided or incorporated by
reference in this prospectus. We have not, and the underwriters have not,
authorized any other person to provide you with different information. This
prospectus is not an offer to sell, nor is it seeking an offer to buy, these
securities in any state where the offer or sale is not permitted. The
information in this prospectus is complete and accurate as of the date on the
front cover, but the information may have changed since that date.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

         We make certain forward-looking statements in this prospectus and in
the documents incorporated by reference into this prospectus that are based upon
our current expectations and projections about current events. We intend these
forward-looking statements to be covered by the safe harbor provisions for
forward-looking statements contained in the Private Securities Litigation Reform
Act of 1995, and we are including this statement for purposes of these safe
harbor provisions. You can identify these statements from our use of the words
"may," "will," "should," "could," "would," "plan," "potential," "estimate,"
"project," "believe," "intend," "anticipate," "expect," "target" and similar
expressions. These forward-looking statements include statements relating to:

         o    our goals, intentions and expectations;

         o    our business plans and growth strategies; and

         o    estimates of our risks and future costs and benefits.

         These forward-looking statements are subject to significant risks,
assumptions and uncertainties, including among other things, changes in general
economic and business conditions and the risks and other factors set forth in
the "Risk Factors" section beginning on page 13.

         Because of these and other uncertainties, our actual future results,
performance or achievements, or industry results, may be materially different
from the results indicated by these forward-looking statements. In addition, our
past results of operations do not necessarily indicate our future results. You
should not place undue reliance on any forward-looking statement, which speak
only as of the date they were made. We will not update these forward-looking
statements, even though our situation may change in the future, unless we are
obligated to do so under the federal securities laws. We qualify all of our
forward-looking statements by these cautionary statements.

                                       i



                               PROSPECTUS SUMMARY

         The items in the following summary are described in more detail later
in this prospectus or in the other information incorporated by reference into
this prospectus. This summary provides an overview of selected information and
does not contain all of the information you should consider. Therefore, you
should also read the more detailed information included in this prospectus, our
consolidated financial statements and the other information that is incorporated
by reference in this prospectus before making a decision to invest in our common
stock. Unless otherwise indicated, the information in this prospectus assumes
that the underwriters will not exercise their option to purchase additional
shares to cover over-allotments.

ABOUT WINTRUST FINANCIAL CORPORATION

         We are a financial holding company headquartered in Lake Forest,
Illinois, with total assets of approximately $4.1 billion at June 30, 2003. We
currently operate seven community banks, primarily in affluent suburbs of
Chicago, which provide community-oriented, personal and commercial banking
services primarily to individuals and small to mid-size businesses through 32
banking facilities. Each of our banks provides a full complement of commercial
and consumer loan and deposit products and services. We provide wealth
management services through our trust company, investment adviser and
broker-dealer subsidiaries to customers, primarily in the Midwest, as well as to
customers of our banks. In addition, we are involved in specialty lending
through a number of operating subsidiaries or divisions of certain of our banks.
Our specialty lending niches include one of the five largest, based on
management's estimates, commercial insurance premium finance companies in the
United States; a company which provides accounts receivable financing and
administrative services to the temporary staffing industry; and an indirect auto
lending business which purchases loans through Chicago-area automobile
dealerships.

FINANCIAL SUMMARY

         We have grown from $1.3 billion in assets at December 31, 1998 to $4.1
billion in assets at June 30, 2003 and our diluted earnings per share have
increased at a compound annual growth rate of 32% over the five-year period
ended December 31, 2002. The following table highlights the financial
performance of our organization for the five-year period ended December 31, 2002
and six-month periods ended June 30, 2003 and June 30, 2002.



                                AS OF OR FOR THE
                                SIX MONTHS ENDED
                                    JUNE 30,                    AS OF OR FOR THE YEAR ENDED DECEMBER 31,
                                ----------------         ------------------------------------------------------
                                2003        2002         2002         2001        2000         1999        1998
                                ----        ----         ----         ----        ----         ----        ----
                                                 (DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)
                         


Total revenue............     $  91,780  $   73,108   $  158,800   $  102,812  $   79,306   $   57,542  $   44,839
Net income...............        17,282      12,669       27,875       18,439      11,155        9,427       6,245
Earnings per share
   (diluted).............          0.94        0.77         1.60         1.27        0.83         0.73        0.49
Total assets.............     4,132,394   3,219,400    3,721,555    2,705,422   2,102,806    1,679,382   1,348,048
Loans....................     2,896,148   2,308,945    2,556,086    2,018,479   1,547,596    1,270,126     974,031
Mortgage loans held-for-
   sale.................         84,643      27,735       90,446       42,904      10,424        8,123      18,031
Total deposits...........     3,419,946   2,608,507    3,089,124    2,314,636   1,826,576    1,463,622   1,229,154
Common shareholders'
   equity................       249,399     205,999      227,002      141,278     102,276       92,947      75,205
Return on average assets.          0.90%       0.88%        0.87%        0.79%       0.60%        0.63%       0.53%
Return on average equity.         14.74%      15.85%       14.76%       15.24%      11.51%       11.58%       8.68%


                                       1



         The following table shows the compound annual growth rates we achieved
over the one-, two-, three-, four- and five-year periods ended December 31,
2002.



                                                        COMPOUND ANNUAL GROWTH RATES
                                        1 YEAR        2 YEAR       3 YEAR        4 YEAR       5 YEAR
                                        ------        ------       ------        ------       ------
                                                                               
Total revenue.....................       54.5%        41.5%         40.3%        37.2%         38.0%
Net income........................       51.2         58.1          43.5         45.4          41.9
Earnings per share (diluted)......       26.0         38.8          29.9         34.4          32.0
Total assets......................       37.6         33.0          30.4         28.9          28.7
Loans.............................       26.6         28.5          26.3         27.3          29.5
Total deposits....................       33.5         30.0          28.3         25.9          27.5
Common shareholders' equity.......       60.7         49.0          34.7         31.8          27.0


COMMUNITY BANKING

         Each of our existing banking subsidiaries was founded as a de novo, or
new, banking organization within the last approximately twelve years. Our
financial performance has been and continues to be affected by costs associated
with growing market share in deposits and loans, opening new banks and branch
facilities, and building an experienced management team. Our recent financial
performance generally reflects the improved profitability of our operating
subsidiaries as they mature, offset by the costs of establishing new banks and
opening new branch facilities. Our experience has been that it generally takes
from 13 to 24 months for new banks to first achieve operational profitability
depending on the number and timing of branch facilities added.

         The following table provides information regarding each of our existing
banks as of June 30, 2003.



                                                                  TOTAL ASSETS       NUMBER OF
                      BANK                     DATE OPENED       (IN THOUSANDS)      FACILITIES
    --------------------------------------   --------------      --------------     ------------
                                                                            
    Lake Forest...........................    December 1991        $1,011,051            7
    Hinsdale..............................     October 1993           688,015            5
    North Shore Community.................    September 1994          817,750            7
    Libertyville..........................     October 1995           540,577            5
    Barrington............................    December 1996           488,672            2
    Crystal Lake..........................    December 1997           356,999            5
    Northbrook............................    November 2000           217,091            1


         We are in the process of organizing our eighth de novo bank in Beverly,
a residential neighborhood on the southwest side of Chicago, which we expect to
open during 2003. In addition, we recently announced plans to acquire two
existing community-oriented banks, both relatively newly formed de novo banks.
One of the banks opened in 1995 and the other opened in 2001. Each of these
banks has two banking offices, all located in northwest suburban Chicago.
Combined, the two banks had total assets of approximately $178 million at June
30, 2003. Both of the acquisitions are expected to close during the fourth
quarter of 2003. See "Recent Developments."

WEALTH MANAGEMENT SERVICES

         We currently offer a full range of wealth management services through
four separate subsidiaries, including trust and investment services, asset
management and securities brokerage services marketed primarily under the Wayne
Hummer name. We acquired the Wayne Hummer operations, based in the Chicago area,
in February 2002. Wayne Hummer Investments, our broker-dealer subsidiary, has
been in operation since 1931.

                                       2



         Through Wayne Hummer Trust Company we offer trust and investment
services to existing bank customers and are also targeting small to mid-size
businesses and affluent individuals whose needs command the personalized
attention offered by our experienced trust professionals. Assets under
administration at the trust company were approximately $485.3 million at June
30, 2003.

         Through Wayne Hummer Investments, a registered broker-dealer, we
provide a full range of private client and securities brokerage services to
approximately 35,000 clients, located primarily in the Midwest. Client assets at
the brokerage firm were approximately $4.2 billion at June 30, 2003. Focused
Investments, LLC, a broker-dealer and wholly-owned subsidiary of Wayne Hummer
Investments, provides a full range of investment services to clients through a
network of relationships with community-based financial institutions primarily
in Illinois.

         Wayne Hummer Asset Management Company, a registered investment adviser,
provides money management services and advisory services to individuals and
institutional accounts as well as four proprietary mutual funds, and also
provides portfolio management and financial supervision for a wide range of
pension and profit-sharing plans. We acquired Lake Forest Capital Management
Company, a registered investment adviser, in February 2003. Lake Forest Capital
Management Company is operating as a separate division of Wayne Hummer Asset
Management Company. At June 30, 2003, individual accounts managed by Wayne
Hummer Asset Management Company, including the accounts of Lake Forest Capital
Management Company, totaled approximately $704.9 million, while the four managed
mutual funds had approximately $309.8 million in total assets.

SPECIALTY LENDING

         We conduct our specialty lending businesses through indirect non-bank
subsidiaries and divisions of our banks.

         Through First Insurance, our most significant specialized lending
niche, we make loans to businesses to finance the insurance premiums they pay on
their commercial insurance policies. The loans are originated by First Insurance
Funding working through independent medium and large insurance agents and
brokers located throughout the nation. The insurance premiums we finance are
primarily for commercial customers' purchases of liability, property and
casualty and other commercial insurance. This lending involves relatively rapid
turnover of the loan portfolio and high volume of loan originations. Because of
the indirect nature of this lending and because the borrowers are located
nationwide, this segment may be more susceptible to third party fraud. The
majority of these loans are purchased by our banks in order to more fully
utilize their lending capacity. These loans generally provide the banks higher
yields than alternative investments. Since the second quarter of 1999, we have
also been selling some of the loan originations to an unrelated third party with
servicing retained. First Insurance originated $1.1 billion in loan (premium
finance receivables) volume in the first six months of 2003 compared to $837.4
million in the first six months of 2002.

         Through Tricom, Inc. we provide high-yielding, short-term accounts
receivable financing and value-added, outsourced administrative services, such
as data processing of payrolls, billing and cash management services, to the
temporary staffing industry. Tricom's clients, located throughout the United
States, provide staffing services to businesses in diversified industries.
During the first six months of 2003, Tricom processed payrolls with associated
client billings of approximately $142.2 million compared to $108.3 million
during the first six months of 2002.

         We engage in other specialty lending through divisions of our banks,
including indirect auto lending which we conduct through a division of Hinsdale
Bank, medical and municipal equipment leasing, small aircraft lending, mortgage
broker warehouse lending and loans to condominium, homeowner and community
associations. These other specialty loans and leases together comprised
approximately 11%

                                       3


of our loan and lease portfolio at June 30, 2003. The indirect automobile loans
are diversified among many individual borrowers, secured by new and used
automobiles and are generated by a network of automobile dealers located in the
Chicago area with which we have established relationships. Like other consumer
loans, the indirect auto loans are subject to the banks' established credit
standards. We regard substantially all of these loans as prime quality loans.
Management continually monitors the dealer relationships to deter third party
fraud, and the banks are not dependent on any one dealer as a source of such
loans. At June 30, 2003, we had $167.2 million of indirect auto loans which
comprised approximately 6% of our loan portfolio. Management is not pursuing
growth in this segment and anticipates that this portfolio will comprise a
smaller portion of the net loan portfolio in the future.

OPERATIONAL STRATEGY

         Since our first bank was opened in 1991, we have been committed to the
same fundamental operational strategy, the key elements of which include the
following:

         o        MAINTAINING DECISION-MAKING AUTHORITY LOCALLY WITHIN EACH OF
                  OUR OPERATING SUBSIDIARIES AND PROVIDING A HIGH LEVEL OF
                  PERSONAL AND PROFESSIONAL SERVICE. Our community banking
                  philosophy is driven by our emphasis on local independence and
                  decision-making authority within each of our banks. While
                  senior management of Wintrust provides expertise to each of
                  our subsidiaries in the areas of capital planning, long-term
                  strategic planning, marketing and advertising, financial
                  management, investment and asset/liability management, and
                  technology, the separate management teams of each of the
                  banks, as well as First Insurance, Wayne Hummer Trust Company,
                  Tricom and the Wayne Hummer Companies have full managerial
                  responsibilities for customer service and the ongoing
                  day-to-day operations of their respective organizations,
                  subject to the oversight of our Board of Directors and the
                  boards of our subsidiaries. Our operating subsidiaries enjoy
                  the competitive advantages of being able to tailor products
                  and services to meet the differing needs of the customers that
                  they serve, to quickly make decisions affecting customers, and
                  to participate actively in their communities.

         o        EMPLOYING FEWER, BUT HIGHLY QUALIFIED AND PRODUCTIVE
                  INDIVIDUALS AT RELATIVELY HIGH COMPENSATION RATES AND FOCUSING
                  ON LOW NET OVERHEAD RATIOS. Key to our growth and
                  profitability is our management's extensive experience in
                  providing community banking and financial services, and
                  retaining highly qualified managers is critical to our
                  strategy. Our banks' presidents and chief executive officers
                  were selected not only for their years of banking experience
                  but also for their business development skills and their
                  strong ties to the communities they serve. Our practice of
                  employing fewer, but highly qualified and productive
                  individuals at all levels of the organization is key to
                  maintaining a decentralized management structure. Although our
                  management compensation levels may be relatively high, we
                  believe our organizational structure allows us to continue to
                  improve and maintain favorable net overhead ratios as the
                  banks, First Insurance, Wayne Hummer Trust Company and Tricom
                  mature.

         o        MARKETING INNOVATIVE DEPOSIT AND LOAN PRODUCTS. Our banks
                  offer local residents competitive retail products designed to
                  attract customers and to provide the banks with the
                  opportunity to introduce and cross-sell their full range of
                  personalized banking services. Each of our banks has developed
                  a strong customer base within its communities through the
                  utilization of creative community-oriented marketing programs.
                  Our banks market their products aggressively through newspaper
                  and other advertising, special promotions and frequently
                  sponsored community events. While competitive pricing may
                  create pressure on our net interest margin at times, to be
                  more responsive to the needs of consumers in their

                                       4


                  specific markets, the banks have also introduced a variety of
                  deposit and loan products to appeal to the unique needs of
                  different types of bank customers, such as different age
                  groups and other special segments of the target markets. In
                  addition, each of our banks has a large board of directors
                  comprised of experienced business persons and other
                  individuals prominent within their respective communities who
                  assist the banking officers with business development.

         o        PURSUING A NUMBER OF SPECIALTY LENDING NICHES. We currently
                  finance loans in several different specialty lending niches to
                  more fully utilize our lending capacity, to diversify our loan
                  portfolio, and to enhance the profitability of our banks. In
                  addition to premium finance loans originated by First
                  Insurance, short-term accounts receivables financed by Tricom,
                  and indirect auto loans, we also engage in mortgage warehouse
                  lending, medical and municipal equipment leasing, homeowners
                  and condominium association lending and small aircraft
                  lending. Loans in our specialty lending niches tend to be
                  higher yielding than other commercial and consumer loans in
                  our banks' portfolios, but may involve greater credit risks
                  than generally associated with loan portfolios of more
                  traditional community banks due to marketability of the
                  collateral or because we do not have direct customer
                  relationships with the underlying borrowers.

         o        FOCUS ON GENERATING FEE INCOME TO AUGMENT NET INTEREST INCOME.
                  During 2002 and the first half of 2003, we generated fee
                  income from a variety of sources including the origination and
                  sale of mortgage loans, account service charges, trust, asset
                  management and brokerage fees, premium income from selling
                  covered call options on fixed income securities we own, as
                  well as gains on sales of premium finance receivables and
                  securities. In addition, we earn administrative fees at Tricom
                  related to its payroll processing business. Non-interest
                  income as a percentage of total revenue increased to 38% for
                  the year ended December 31, 2002, from 28% in 2001 and was 40%
                  for the first six months of 2003.

GROWTH STRATEGY

         Key elements of our growth strategy include the following:

         o        INTERNAL GROWTH OF OUR EXISTING BANKS. Due to our de novo
                  strategy, we believe we have not yet realized the full deposit
                  and asset generation potential in the communities now served
                  by our existing banking facilities. We believe we can leverage
                  our existing infrastructure to support additional business
                  while maintaining a high level of personalized customer
                  service and responsiveness. As consolidation and the trend
                  toward nationwide franchises continue in the financial
                  services industry, management expects that more individuals
                  and small businesses will become disenchanted with the
                  perceived lower level of service offered by the larger
                  institutions, providing continuing market share opportunity
                  for us. We may from time to time compete for deposits,
                  particularly in our newer markets, with aggressive pricing,
                  which may reduce our net interest margin. With management's
                  focus on balancing further asset growth with earnings growth,
                  our current strategy is to continue less aggressive deposit
                  pricing at those banks with significant market share and more
                  established customer bases.

         o        EXPANDING INTO ATTRACTIVE MARKETS WITH LIMITED LOCAL BANKING
                  COMPETITION. We plan to continue our geographic expansion by
                  leveraging our existing banks and opening new branch
                  facilities in nearby communities where management believes
                  targeted customers would be attracted to a community banking
                  alternative. We have plans to add four to five new branches of
                  existing banks over the next 12 months. We also intend to
                  continue the formation of additional de novo banks in
                  attractive markets in and around the Chicago metropolitan
                  area. We are currently organizing our eighth de novo bank in
                  Beverly, a


                                       5


                  residential neighborhood on the southwest side of Chicago,
                  which we expect to open during 2003. We will continue to be
                  impacted by start-up costs related to this bank, as well as
                  additional de novo bank and branch formations that we expect
                  to undertake in the future.

                  In addition, part of our strategy is to pursue potential
                  acquisitions of other community-oriented banks that are
                  already operating in desirable markets in the greater Chicago
                  metropolitan area. We recently announced the signing of
                  definitive agreements to acquire two banks, both relatively
                  newly formed, with banking locations in four communities in
                  northwest suburban Chicago that we do not now serve. See
                  "Recent Developments." In pursuing acquisitions, we face
                  potential competition from other bidders, and we have not
                  always been successful in acquiring other banks due to seller
                  price expectations or other factors. These and other
                  acquisitions, if any, could have a short-term dilutive effect
                  on earnings per share although the two pending acquisitions
                  are not expected to have any material impact on 2003 or 2004
                  earnings per share.

         o        AUGMENTING THE LOAN PORTFOLIO WITH OUR SPECIALTY LENDING
                  NICHES TO ALLOW THE BANKS TO MORE FULLY UTILIZE THEIR LENDING
                  CAPACITY AND ADDING RELATED FINANCIAL SERVICES BUSINESSES TO
                  INCREASE FEE INCOME. Our specialty lending niches have
                  enhanced the profitability of our community banks by
                  optimizing their earning asset base and allowing them to
                  diversify their loan portfolios. We plan to continue to build
                  our sales staff at First Insurance to further increase loan
                  volume in our premium finance business, seeking to increase
                  our market penetration in selected geographic markets. Certain
                  of our related financial services businesses also contribute
                  to higher fee income, such as administrative service fees
                  earned by Tricom for payroll processing. We may pursue
                  acquisitions or development of additional specialty lending
                  businesses engaged in asset generation suitable for bank
                  investment and/or secondary market sales. We may also pursue
                  acquisitions or development of related financial services
                  businesses to augment fee income. Management intends to
                  continue to explore various commercial and consumer finance
                  activities and to seek attractive potential acquisition
                  candidates. Acquisitions, if any, could have a short-term
                  dilutive effect on earnings per share.

         o        GROWTH OF WEALTH MANAGEMENT SERVICES PROVIDED TO SMALL AND
                  MID-SIZED BUSINESSES AND AFFLUENT INDIVIDUALS. Our
                  acquisitions of the Wayne Hummer Companies in 2002 and Lake
                  Forest Capital Management Company in February 2003
                  significantly expanded our wealth management customer base and
                  have enabled us to diversify our revenue stream. As part of
                  our strategy to build and grow our wealth management business,
                  we are continuing to recruit talented brokers, cross-market
                  our expanded base of brokerage and investment management
                  products and services to our banking clients while offering
                  trust services and estate planning products, as well as
                  traditional banking services, to wealth management customers.
                  In April 2003, we hired Thomas M. McDonald, with more than 30
                  years of experience in the investment services industry, as
                  the new president and chief executive officer of Wayne Hummer
                  Investments to further enhance the leadership of this segment
                  of our business.

OFFICE LOCATION

         Our principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045-1951, and our telephone number is (847) 615-4096.


                                       6



RECENT DEVELOPMENTS

         We recently announced two planned acquisitions of community-oriented
banks. We believe that together the acquisitions provide an attractive
opportunity to expand into the northwest Chicago metropolitan area, in suburban
markets we consider desirable. Both transactions are subject to approval by
regulators, approval by the target company's shareholders and other closing
conditions. We currently expect to close these transactions in the fourth
quarter of 2003. We do not expect these transactions to have a material impact
on our 2003 or 2004 earnings per share or our regulatory capital ratios.

         On July 2, 2003, we announced the signing of a definitive agreement to
acquire Advantage National Bancorp, Inc., the parent company of Advantage
National Bank, in a stock merger transaction, with an aggregate purchase price
of approximately $24.4 million, assuming all Advantage warrants are exercised.
The number of shares to be issued in the merger will be determined at closing
based on a floating exchange ratio. Depending on the average price of our common
stock at the closing of the merger, we may issue up to 1,049,304 shares of our
stock in the merger. Advantage National Bank, a de novo bank that began
operations in January 2001, has one location in Elk Grove Village and one
location in Roselle, Illinois, both northwest suburbs of Chicago. Advantage had
total assets of approximately $104 million at June 30, 2003.

         On August 7, 2003, we announced the signing of a definitive agreement
to acquire Village Bancorp, Inc. in a stock merger transaction, with an
aggregate purchase price of approximately $9.0 million. The number of shares to
be issued in the merger will be determined at closing based on a floating
exchange ratio. Depending on the average price of our common stock at the
closing of the merger, we may issue up to 360,000 shares of our stock in the
merger. Village is the parent company of Village Bank and Trust-Arlington
Heights that has one location in each of Arlington Heights and Prospect Heights,
Illinois. Village Bank began operations as a de novo bank in 1995. Village had
total assets of approximately $74 million as of June 30, 2003.


                                       7

                                  THE OFFERING


                                                            
Common stock offered.......................................     1,000,000 shares

Offering price per share...................................     $

Common stock to be outstanding
   after the offering......................................     18,472,036 shares(1)

Use of proceeds............................................     We intend to use the net proceeds of this offering
                                                                to increase the capital at our banks to pursue
                                                                growth opportunities and for general corporate
                                                                purposes.

Risk Factors...............................................     See "Risk Factors" beginning on page 13 and other
                                                                information included in this prospectus for a
                                                                discussion of factors you should consider carefully
                                                                before deciding to invest in our common stock.

Nasdaq National Market symbol..............................     WTFC

--------------------

(1)      The number of shares shown to be outstanding after the offering is
         based on the number of shares of our common stock outstanding as of
         August 29, 2003, and does not include 4,131,501 shares reserved for
         issuance under our stock incentive plan and other compensation plans or
         upon the exercise of outstanding warrants, or up to a maximum of
         approximately 1.4 million shares that we expect to issue in connection
         with our two pending acquisitions. As of August 29, 2003, we had
         outstanding options and restricted stock unit awards relating to
         2,965,543 shares and warrants to purchase 262,248 shares of our common
         stock.




                                       8



                       SUMMARY CONSOLIDATED FINANCIAL DATA

         The summary consolidated financial data presented below as of or for
each of the years in the five-year period ended December 31, 2002, are derived
from our audited historical financial statements. The summary data presented
below as of or for the six-month periods ended June 30, 2003 and 2002, are
derived from unaudited consolidated financial statements. In our opinion, all
adjustments, consisting only of normal recurring adjustments, necessary for a
fair statement of results as of or for the six-month periods have been included.
Per share amounts have been adjusted to reflect the 3-for-2 stock split effected
as a stock dividend effective as of March 14, 2002. This information should be
read in conjunction with "Management's Discussion and Analysis of Financial
Condition and Results of Operations" and the consolidated financial statements
and the notes thereto incorporated by reference into this prospectus from our
Annual Report on Form 10-K for the fiscal year ended December 31, 2002, and our
Quarterly Report on Form 10-Q for the period ended June 30, 2003. Results for
past periods are not necessarily indicative of results that may be expected for
any future period, and results for the six-month period ended June 30, 2003 are
not necessarily indicative of results that may be expected for the entire year
ending December 31, 2003.



                              SIX MONTHS ENDED
                                  JUNE 30,                             YEAR ENDED DECEMBER 31,
                             --------------------- --------------------------------------------------------------
                             2003(1)     2002(2)      2002(2)       2001         2000        1999         1998
                             -------     -------      -------       ----         ----        ----         ----

                                                  (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS)
                                                                                    
STATEMENT OF INCOME
   DATA:
Total interest income..     $  96,504    $  86,509   $ 182,233    $ 166,455    $ 148,184   $ 109,331    $  87,979
Total interest expense.        41,572       39,924      84,105       92,441       87,184      61,597       51,215
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
   Net interest income.        54,932       46,585      98,128       74,014       61,000      47,734       36,764
Provision for loan
   losses..............         5,493        4,831      10,321        7,900        5,055       3,713        4,297
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
   Net interest income
      after provision
      for loan losses..        49,439       41,754      87,807       66,114       55,945      44,021       32,467
Non-interest Income:
   Gain on sale of
      premium finance
      receivables......         2,270        1,594       3,374        4,564        3,831       1,033           --
   Fees on mortgage
      loans sold.......         9,142        3,951      12,259        7,831        2,911       3,206        5,569
   Wealth management
      fees.............        12,953       12,001      25,229        1,996        1,971       1,171          788
   Service charges on
      deposit accounts.         1,722        1,491       3,121        2,504        1,936       1,562        1,065
   Administrative
      services revenues         2,159        1,753       3,501        4,084        4,402         996           --
   Premium finance
      defalcation-partial
      settlement(3)....            --        1,250       1,250           --           --          --           --
   Securities (losses)
      gains, net.......           606         (153)        107          337          (40)          5           --
   Other...............         7,996        4,636      11,831        7,482        3,295       1,835          653
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
      Total
        non-interest
        income.........        36,848       26,523      60,672       28,798       18,306       9,808        8,075
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------


(See footnotes on page 11)

                                       9




                              SIX MONTHS ENDED
                                  JUNE 30,                             YEAR ENDED DECEMBER 31,
                             --------------------- --------------------------------------------------------------
                             2003(1)     2002(2)      2002(2)       2001         2000        1999         1998
                             -------     -------      -------       ----         ----        ----         ----

                                                  (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS)
                                                                                    
Non-interest Expense:
   Salaries and
      employee benefits     $  35,715 $     28,762   $  63,442    $  35,628    $  28,119   $  20,808    $  18,944
   Equipment expense...         3,758        3,526       7,191        6,297        5,101       3,199        2,221
   Occupancy expense,
      net..............         3,785        3,153       6,691        4,821        4,252       2,991        2,435
   Data processing.....         2,079        2,056       4,161        3,393        2,837       2,169        1,676
   Advertising and
      marketing........         1,043        1,057       2,302        1,604        1,309       1,402        1,612
   Professional fees...         1,704        1,296       2,801        2,055        1,681       1,203        1,654
   Amortization of
      intangibles......           298          117         324          685          713         251          120
   Premium finance
      defalcation(3)...            --           --          --           --        4,320          --           --
   Other non-interest
      expenses.........        11,038        8,618      19,072       11,300        9,471       7,655        7,171
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
      Total
        non-interest
        expense........        59,420       48,585     105,984       65,783       57,803      39,678       35,833
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
Income before taxes
   and cumulative
   effect of
   accounting change...        26,867       19,692      42,495       29,129       16,448      14,151        4,709
Income tax expense
   (benefit)...........         9,585        7,023      14,620       10,436        5,293       4,724       (1,536)
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
Income before
   cumulative effect
   of accounting change        17,282       12,669      27,875       18,693       11,155       9,427        6,245
Cumulative effect of
   change in
   accounting for
   derivatives, net of
   tax.................            --           --          --         (254)          --          --           --
                            ---------    ---------   ---------    ---------    ---------   ---------    ---------
   Net income..........     $  17,282    $  12,669   $  27,875    $  18,439    $  11,155   $   9,427    $   6,245
                            =========    =========   =========    =========    =========   =========    =========
COMMON SHARE DATA:
Earnings per share:
   Basic...............     $    1.00    $    0.82   $    1.71    $    1.34    $    0.85   $    0.76    $    0.51
   Diluted.............          0.94         0.77        1.60         1.27         0.83        0.73         0.49
Cash dividends per
   common share(4).....          0.08         0.06        0.12         0.093        0.067         --           --
Book value per share...         14.31        12.15       13.19         9.72         7.92        7.06         6.15
Weighted average
   common shares
   outstanding:
   Basic...............        17,360       15,513      16,334       13,734       13,066      12,373       12,212
   Diluted.............        18,473       16,526      17,445       14,545       13,411      12,837       12,742

SELECTED FINANCIAL
   CONDITION DATA (AT
   END OF PERIOD):
Total assets...........    $4,132,394   $3,219,400  $3,721,555   $2,705,422   $2,102,806  $1,679,382   $1,348,048
Loans..................     2,896,148    2,308,945   2,556,086    2,018,479    1,547,596   1,270,126      974,031
Mortgage loans held-
   for-sale...........         84,643       27,735      90,446       42,904       10,424       8,123       18,031
Total deposits.........     3,419,946    2,608,507   3,089,124    2,314,636    1,826,576   1,463,622    1,229,154
Notes payable..........        26,000       58,650      44,025       46,575       27,575       8,350           --
Subordinated notes.....        50,000           --      25,000           --           --          --           --
Long term debt - trust
   preferred securities        76,816       51,050      50,894       51,050       51,050      31,050       31,050
Total shareholders'
   equity..............       249,399      205,999     227,002      141,278      102,276      92,947       75,205


(See footnotes on following page)


                                       10




                              SIX MONTHS ENDED
                                  JUNE 30,                             YEARS ENDED DECEMBER 31,
                             --------------------- --------------------------------------------------------------
                             2003(1)     2002(2)      2002(2)       2001         2000        1999         1998
                             -------     -------      -------       ----         ----        ----         ----

                                                                                    
SELECTED FINANCIAL
   RATIOS AND OTHER
   DATA:
Performance Ratios:
   Net interest
      margin(5)(6)(7)..          3.14%        3.52%       3.34%        3.49%        3.66%       3.54%        3.43%
   Net interest
      spread(5)(8)(9)..          2.92         3.22        3.06         3.08         3.29        3.23         3.00
   Non-interest income
      to average
      assets(5)........          1.92         1.85        1.89         1.24         0.99        0.66         0.69
   Non-interest
      expense to
      average
      assets(3)(5).....          3.10         3.38        3.30         2.83         3.12        2.65         3.04
   Net overhead
      ratio(3)(5)(10)..          1.18         1.54        1.41         1.59         2.13        2.00         2.36
   Efficiency
      ratio(3)(11)(7)..         64.86        65.96       66.41        63.66        72.33       68.63        79.75
   Return on average
      assets(3)(5).....          0.90         0.88        0.87         0.79         0.60        0.63         0.53
   Return on average
      equity(3)(5).....         14.74        15.85       14.76        15.24        11.51       11.58         8.68
   Average
      loan-to-average
      deposit ratio....          86.1         90.4        88.5         87.4         87.7        86.6         80.1
   Dividend payout
      ratio(4)(5)......           8.5          7.7         7.5          7.4          8.0          --           --
Asset Quality Ratios:
   Non-performing
      loans to total
      loans............          0.47%        0.48%       0.49%        0.64%        0.63%       0.55%        0.56%
   Allowance for loan
      losses to:
      Total loans......          0.74         0.69        0.72         0.68         0.67        0.69         0.72
      Non-performing
        loans..........        156.42       143.39      146.63       105.63       107.75      126.10       129.66
   Net charge-offs to
      average
      loans(3)(5)......          0.19         0.23        0.24         0.26         0.24        0.19         0.28
   Non-performing
      assets to total
      assets...........          0.35         0.37        0.34         0.48         0.46        0.41         0.45
Other data at end of
   period:
   Number of banking
      facilities.......            32           31          31           29           28          24           21

---------------------
(1)      We completed our acquisition of Lake Forest Capital Management Company
         on February 1, 2003. The results for the six months ended June 30, 2003
         include the results of Lake Forest Capital Management Company since
         that date.
(2)      We completed our acquisition of the Wayne Hummer Companies effective as
         of February 1, 2002. The results for the six months ended June 30, 2002
         and year ended December 31, 2002 include the results of the Wayne
         Hummer Companies since February 1, 2002.
(3)      In 2000, we recorded a $4.3 million pre-tax charge ($2.6 million
         after-tax) related to a fraudulent loan scheme perpetrated against our
         premium finance subsidiary. The amount of this charge was not included
         in loans charged-off because a lending relationship had never been
         established. In the first quarter of 2002, we recovered $1.25 million
         (pre-tax) of this amount ($754,000 after-tax).
(4)      We declared our first semi-annual dividend payment in January 2000.
         Dividend data reflected for the interim periods reflect semi-annual,
         not quarterly, dividends.
(5)      Certain financial ratios for interim periods have been annualized.
(6)      Net interest income on a tax-equivalent basis divided by average
         interest-earning assets.
(7)      See "Supplemental Financial Measures/Ratios" on page 12 for a
         reconciliation of net interest income to net interest income on a tax
         equivalent basis.
(8)      Calculated on a tax-equivalent basis.
(9)      Yield earned on average interest-earning assets less rate paid on
         average interest-bearing liabilities.
(10)     Non-interest expense less non-interest income divided by average total
         assets.
(11)     Non-interest expense (excluding non-recurring items) divided by the sum
         of net interest income on a tax equivalent basis plus non-interest
         income (excluding securities gains and losses).




                                       11


SUPPLEMENTAL FINANCIAL MEASURES/RATIOS

         Certain non-GAAP performance measures and ratios are used by management
to evaluate and measure our performance. These include taxable-equivalent net
interest income (including its individual components), net interest margin
(including its individual components), and the efficiency ratio. Management
believes that these measures and ratios provide users of our financial
information a more accurate view of the performance of the interest-earning
assets and interest-bearing liabilities and of our operating efficiency for
comparative purposes than the most directly comparable GAAP measures. Other
financial holding companies may define or calculate these measures and ratios
differently. See the table below for supplemental data and the corresponding
reconciliation to GAAP financial measures for the six months ended June 30, 2003
and 2002, and for the years ended December 31, 1998 through 2002.

         Management reviews yields on certain asset categories and the net
interest margin of the company, and our banking subsidiaries, on a fully
taxable-equivalent basis or "FTE." In this non-GAAP presentation, net interest
income is adjusted to reflect tax-exempt interest income on an equivalent
before-tax basis. This measure ensures comparability of net interest income
arising from both taxable and tax-exempt sources. Net interest income on a
taxable-equivalent basis is also used in the calculation of our efficiency
ratio. The efficiency ratio, which is calculated by dividing non-interest
expense by total taxable-equivalent net revenue (less securities gains or
losses), measures how much it costs to produce one dollar of revenue. Securities
gains or losses are excluded from this calculation to better match revenue from
daily operations to operational expenses.

         The following table reconciles the GAAP calculations to the financial
measures and ratios used by management as discussed above.




                               SIX MONTHS ENDED
                                   JUNE 30,                            YEARS ENDED DECEMBER 31,
                             ---------------------    ---------------------------------------------------------
                               2003        2002        2002         2001         2000        1999         1998
                               ----        ----        ----         ----         ----        ----         ----
                                                                (IN THOUSANDS)
                                                                                     
(A) INTEREST INCOME
   (GAAP)...............      $96,504      $86,509    $182,233     $166,455     $148,184    $109,331      $87,979
   FTEA - Loans(1)......          265          356         685          793          518         259           95
   FTEA - Liquidity
      management
      assets(1).........          134           43         209           65           48          15           --
   FTEA - Other earning
      assets(1).........           39           --          --           --           --          --           --
                              -------      -------    --------     --------     --------    --------      -------
   Interest income - FTE       96,942       86,908     183,127      167,313      148,750     109,605       88,074
(B) INTEREST EXPENSE
   (GAAP)...............       41,572       39,924      84,105       92,441       87,184      61,597       51,215
                              -------      -------    --------     --------     --------    --------      -------
   Net interest
      income - FTE......      $55,370      $46,984     $99,022      $74,872      $61,566     $48,008      $36,859
                              -------      -------    --------     --------     --------    --------      -------
(C) NET INTEREST INCOME
   (GAAP) (A MINUS B)...      $54,932      $46,585     $98,128      $74,014      $61,000     $47,734      $36,764
(D) NET INTEREST MARGIN
   (GAAP)...............         3.12%        3.49%       3.31%        3.45%        3.63%       3.52%        3.42%
   Net interest
      margin - FTE......         3.14         3.52        3.34         3.49         3.66        3.54         3.43
(E) EFFICIENCY RATIO
   (GAAP)...............        65.17        66.32       66.79        64.19        72.85       68.96        79.91
   Efficiency ratio -
      FTE...............        64.86        65.96       66.41        63.66        72.33       68.63        79.75

---------------------
(1) FTEA = Fully taxable-equivalent adjustment based on an assumed marginal
    federal tax rate of 35%.




                                       12


                                  RISK FACTORS

         You should carefully consider the following risk factors before you
decide to buy our common stock. You should also consider the other information
in this prospectus, as well as the documents incorporated by reference in this
prospectus.

DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY.

         Our financial results have been and will continue to be impacted by our
strategy of de novo bank formations and branch openings. We have employed this
strategy to build an infrastructure that management believes can support
additional internal growth in our banks' respective markets. We expect to open
our eighth de novo bank in late 2003, and expect to undertake additional de novo
bank formations or branch openings as we expand into additional communities in
and around Chicago. In addition, our pending acquisitions involve relatively
recently formed de novo banks. Based on our experience, management believes that
it generally takes from 13 to 24 months for new banks to first achieve
operational profitability, depending on the number of branch facilities opened,
the impact of organizational and overhead expenses, the start-up phase of
generating deposits and the time lag typically involved in redeploying deposits
into attractively priced loans and other higher yielding earning assets.
However, it may take longer than expected or than the amount of time we have
historically experienced for new banks and/or branch facilities to reach
profitability, and there can be no guarantee that these new banks or branches
will ever be profitable. To the extent we undertake additional de novo bank,
branch and business formations, our level of reported net income, return on
average equity and return on average assets will be impacted by start-up costs
associated with such operations, and we are likely to continue to experience the
effects of higher expenses relative to operating income from the new operations.
These expenses may be higher than we expected or than our experience has shown.

WE COULD ENCOUNTER DIFFICULTIES OR UNEXPECTED DEVELOPMENTS RELATED TO OUR
PENDING ACQUISITIONS.

         The two merger transactions that we have pending are our first bank
acquisitions. Both of these banks operate in markets we have not previously
served. While we currently expect to close both the Advantage and the Village
transactions in the fourth quarter of 2003, subject to receipt of required
regulatory and shareholder approvals, we may not be successful in completing the
acquisitions as planned if, for example, all of the closing conditions are not
met. If we do complete the acquisitions, we may be adversely impacted if we have
difficulty integrating these banks into our organization or if the composition
or quality of the banks' assets or liabilities that we acquire differ
significantly from our expectations. In addition, our net income and earnings
per share could be adversely impacted if we incur greater than anticipated costs
associated with operating these banks, if we have difficulty retaining key
personnel at the banks, or if we are unable to grow the businesses of the banks
as contemplated.

WE DEPEND ON OUR ABILITY TO ATTRACT AND RETAIN KEY PERSONNEL; WE RELY HEAVILY ON
OUR MANAGEMENT TEAM, AND THE UNEXPECTED LOSS OF KEY MANAGERS MAY ADVERSELY
AFFECT OUR OPERATIONS.

         Our success to date has been influenced strongly by our ability to
attract and to retain senior management experienced in banking and financial
services. Retention of senior managers and appropriate succession planning will
continue to be critical to the successful implementation of our strategies. We
have entered into 64 employment contracts with our executive officers, and
certain senior officers who we consider to be key employees. It is also
important as we grow to be able to attract and retain additional qualified
senior and middle management. We do not currently maintain key-man life
insurance policies; however, we do maintain bank-owned life insurance policies
on most of our executive officers to offset liabilities under employment
contracts. The unexpected loss of services of any key management personnel, or
the inability to recruit and retain qualified personnel in the future, could
have an adverse effect on our business and financial results.


                                       13



OUR ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB LOSSES THAT
MAY OCCUR IN OUR LOAN PORTFOLIO.

         Our allowance for loan losses is established in consultation with
management of our operating subsidiaries and is maintained at a level considered
adequate by management to absorb loan losses that are inherent in the
portfolios. At June 30, 2003, our allowance for loan losses was 156.42% of total
non-performing loans and 0.74% of total loans. The amount of future losses is
susceptible to changes in economic, operating and other conditions, including
changes in interest rates, that may be beyond our control, and such losses may
exceed current estimates. Rapidly growing and de novo bank loan portfolios are,
by their nature, unseasoned. As a result, estimating loan loss allowances for
our newer banks is more difficult, and therefore the banks may be more
susceptible to changes in estimates, and to losses exceeding estimates, than
banks with more seasoned loan portfolios. Although management believes that the
allowance for loan losses is adequate to absorb losses that may develop in our
existing portfolios of loans and leases, there can be no assurance that the
allowance will prove sufficient to cover actual loan or lease losses in the
future.

OUR PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND COULD EXPOSE
US TO SIGNIFICANT LOSSES.

         Of our total loans at June 30, 2003, 22%, or $625.8 million, were
comprised of commercial insurance premium finance receivables that we generated
through First Insurance. These loans, intended to enhance the average yield of
earning assets of our banks, involve a different, and possibly higher, level of
risk of delinquency or collection than generally associated with loan portfolios
of more traditional community banks. First Insurance also faces unique
operational and internal control challenges due to the relatively rapid turnover
of the premium finance loan portfolio and high volume of new loan originations.
The average term to maturity of these loans is less than 12 months, and the
average loan size when originated is approximately $30,000.

         Because we conduct lending in this segment primarily through
relationships with a large number of unaffiliated insurance agents and because
the borrowers are located nationwide, risk management and general supervisory
oversight may be more difficult than in our banks. We may also be more
susceptible to third party fraud. Acts of fraud are difficult to detect and
deter, and we cannot assure investors that our risk management procedures and
controls will prevent losses from fraudulent activity. For example, in the third
quarter of 2000, we recorded a non-recurring after-tax charge of $2.6 million in
connection with a series of fraudulent loan transactions perpetrated against
First Insurance by one independent insurance agency located in Florida. Although
we have since enhanced our internal controls system at First Insurance, we may
continue to be exposed to the risk of significant loss in our premium finance
business.

         Due to continued growth in origination volume of premium finance
receivables, since the second quarter of 1999, we have been selling some of the
loans First Insurance originates to an unrelated third party. We have recognized
gains on the sales of the receivables, and the proceeds of sales have provided
us with additional liquidity. Consistent with our strategy to be asset driven,
we expect to pursue similar sales of premium finance receivables in the future;
however, we cannot assure you that there will continue to be a market for the
sale of these loans and the extent of our future sales of these loans will
depend on the level of new volume growth in relation to our capacity to retain
the loans within our subsidiary banks' loan portfolios. Because we have a
recourse obligation to the purchaser of premium finance loans that we sell, we
could incur losses in connection with the loans sold if collections on the
underlying loans prove to be insufficient to repay to the purchaser the
principal amount of the loans sold plus interest at the negotiated buy-rate and
if the collection shortfall on the loans sold exceeds our estimate of losses at
the time of sale.


                                       14



OUR STRATEGY OF PURSUING SPECIALTY LENDING NICHES MAY EXPOSE US TO CREDIT RISKS
THAT ARE UNIQUE FOR A COMMUNITY BANKING ORGANIZATION OF OUR SIZE.

         At June 30, 2003, approximately 33% of our total loan portfolio
consisted of loans we make in what we consider to be specialty lending niches.
In addition to our premium finance loans, we engage in indirect auto lending,
accounts receivable financing, mortgage broker warehouse lending, loans to
condominium, homeowner and community associations, and to a much lesser extent,
medical and municipal equipment leasing and small aircraft lending.

         Our portfolio of automobile loans are originated indirectly through
unaffiliated automobile dealers located throughout the Chicago metropolitan
area. At June 30, 2003, our indirect auto loans were $167.2 million and
comprised approximately 6% of our loan portfolio. Because we are lending through
third-party originators, our indirect auto portfolio may be relatively riskier
than direct consumer lending. Also, because the indirect auto loan industry is
highly competitive, the cost of collection and repossession of the underlying
collateral may significantly reduce the profitability of this portfolio,
particularly in a recessionary environment.

         Through Tricom we finance payrolls of companies engaged in the
temporary staffing business. At June 30, 2003, these finance receivables totaled
$24.1 million and represented approximately 1% of our loan portfolio. The
principal source of repayments on the loans we make in this niche are payments
to our borrowers from their customers who are located throughout the United
States. While we employ lockboxes and other cash management techniques to
protect our interests, to the extent third parties fail to pay or fraudulently
engage in the conversion of funds through misuse or nonuse of the lockbox or the
creation of ghost payrolls, we may suffer losses.

         Our lease financing niche may involve a higher degree of credit risk
than mortgage or consumer lending due primarily to the potential for relatively
rapid depreciation of medical equipment and other assets securing leases.
Similarly, in the event of a default of loans originated in our aircraft lending
program, the marketability of the collateral may make it more difficult to
convert this collateral to cash, especially in an adverse economic environment.
In our condominium and homeowner association lending niche, we may face
difficulties in securing repayment from our association borrowers to the extent
they are unable to collect assessments from their members, and we may suffer
losses if we are unable to enforce liens against homeowner properties.

OUR WEALTH MANAGEMENT BUSINESSES ARE VULNERABLE TO FLUCTUATIONS IN THE TRADING
VOLUME AND PRICE LEVELS OF SECURITIES; WE FACE STRONG COMPETITION FOR NEW
BROKERS WE SEEK TO HIRE.

         The success of the strategy we are pursuing to grow our wealth
management business is largely dependent on our ability to identify, hire and
retain talented securities brokers with investment services experience. We face
strong competition for qualified brokers, and many potential candidates are
subject to restrictive covenants with existing employers. If we are unable to
significantly increase the size of our investment services sales force as
planned, we may have difficulty attracting new accounts and increasing assets
under management and may be unable to improve the profitability of this segment
of our business.

         The results of our wealth management subsidiaries depend heavily on
conditions in the financial markets and on economic conditions generally, both
domestically and abroad. Because currently a significant portion of our revenue
in these businesses is derived from commissions, margin interest revenue and
principal transactions, further declines in stock prices, trading volumes or
liquidity could result in the failure of buyers and sellers of securities to
fulfill their settlement obligations, and in the failure of our brokerage
clients to fulfill their credit obligations, which could adversely affect our
profitability.


                                       15



WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

         Our interest income and interest expense are affected by general
economic conditions and by the policies of regulatory authorities, including the
monetary policies of the Federal Reserve. Changes in interest rates may
influence the growth rate of loans and deposits, the quality of the loan
portfolio and loan and deposit pricing. While we have taken measures intended to
manage the risks of operating in a changing interest rate environment, there can
be no assurance that such measures will be effective in avoiding undue interest
rate risk. For example, due to historically low prevailing interest rates,
beginning in late 2001, we moved to an asset/liability position intended to
benefit us in a rising rate scenario. As interest rates declined further over
the last 18 months, we have suffered compression in our net interest margin as a
result of this strategy. However, the significant decline in interest rates to
historic lows has also led to significant increases in mortgage loan origination
volume since 2001. We recorded fees on mortgage loans sold of $9.1 million in
the first six months of 2003 and $12.3 million in 2002, compared to $7.8 million
in 2001. This source of non-interest income is likely to decline in periods of
rising interest rates.

         The success of our covered call option program, which we have used in
effect to hedge our interest rate risk, may also be affected by changes in
interest rates. With the decline in interest rates over the last two years to
historically low levels, we have been able to augment the total return of our
investment securities portfolio by selling call options on fixed-income
securities we own. We recorded fee income of $6.0 million during 2002 compared
to $4.3 million in 2001, from premiums earned on these covered call option
transactions. During the first six months of 2003, we recorded fee income of
$4.8 million on these transactions. In a rising interest rate environment,
particularly if the yield curve remains steep, the amount of premium income we
earn on these transactions will likely decline. In addition, we have decreased
our covered call option activity as rates have increased recently. Our
opportunities to sell covered call options may be limited in the future if rates
continue to rise.

OUR FUTURE SUCCESS IS DEPENDENT ON OUR ABILITY TO COMPETE EFFECTIVELY IN THE
HIGHLY COMPETITIVE BANKING INDUSTRY.

         The financial services business is highly competitive, and we encounter
strong direct competition for deposits, loans and other financial services in
all of our market areas. In recent years, several major bank holding companies
have entered or expanded in the Chicago metropolitan market, and are pursuing
aggressive branching initiatives in the area. Generally, these financial
institutions are significantly larger than we are and have greater access to
capital and other resources. Our ability to compete effectively in the
marketplace is also dependent on our ability to adapt successfully to
technological changes within the banking and financial services industries.

OUR BUSINESS MAY BE ADVERSELY AFFECTED BY THE HIGHLY REGULATED ENVIRONMENT IN
WHICH WE OPERATE.

         We are subject to extensive federal and state legislation, regulation
and supervision. The burden of regulatory compliance has increased under current
legislation and banking regulations and is likely to continue to have or may
have a significant impact on the financial services industry. Recent legislative
and regulatory changes, as well as changes in regulatory enforcement policies
and capital adequacy guidelines, are increasing our costs of doing business and,
as a result, may create an advantage for our competitors who may not be subject
to similar legislative and regulatory requirements. In addition, future
regulatory changes, including changes to regulatory capital requirements, could
have an adverse impact on our future results. Self regulatory organizations,
such as the New York Stock Exchange and the National Association of Securities
Dealers, require our securities brokerage subsidiaries to comply with extensive
rules and regulations, and we could also be adversely affected by applicable
changes in these regulations.


                                       16



SINCE OUR BUSINESS IS CONCENTRATED IN THE CHICAGO METROPOLITAN AREA, A DOWNTURN
IN THE CHICAGO ECONOMY MAY ADVERSELY AFFECT OUR BUSINESS.

         Currently, our lending and deposit gathering activities are
concentrated primarily in the greater Chicago metropolitan area. Our success
depends on the general economic condition of Chicago and its surrounding areas.
Declining economic conditions could reduce our growth rate, impair our ability
to collect loans, and generally affect our financial condition and results of
operations.

THERE IS FLUCTUATION IN THE TRADING MARKET FOR OUR COMMON STOCK; YOU MAY NOT BE
ABLE TO RESELL YOUR SHARES AT OR ABOVE THE PRICE YOU PAY FOR THEM.

         The price of our shares of common stock subject to this offering may be
greater than the market price for our common stock following the offering. The
price of our common stock has been, and will likely continue to be, subject to
fluctuations based on, among other things, economic and market conditions for
financial services companies and the stock market in general, as well as changes
in investor perceptions of our company.

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The maintenance of an active public trading market depends,
however, upon the existence of willing buyers and sellers, the presence of which
is beyond our control or the control of any market maker, and there can be no
assurance that our shareholders will be able to sell their shares at or above
the offering price. A number of shares of our common stock are covered by resale
registration statements. We estimate that there are currently approximately
665,000 of those shares outstanding that have not yet been resold. These
remaining shares may be freely sold from time to time in the market. The market
price of our common stock could drop significantly if shareholders sell or are
perceived by the market as intending to sell large blocks of our shares. In
addition, we have plans to issue up to a maximum of approximately 1.4 million
additional shares of our common stock in two pending bank acquisitions expected
to close during the fourth quarter of 2003.

OUR SHAREHOLDER RIGHTS PLAN AND PROVISIONS IN OUR ARTICLES OF INCORPORATION AND
OUR BY-LAWS MAY DELAY OR PREVENT AN ACQUISITION OF US BY A THIRD PARTY.

         Our board of directors has implemented a shareholder rights plan. The
rights, which are attached to our shares and trade together with our common
stock, have certain anti-takeover effects. The plan may discourage or make it
more difficult for another party to complete a merger or tender offer for our
shares without negotiating with our board of directors or to launch a proxy
contest or to acquire control of a larger block of our shares. If triggered, the
rights will cause substantial dilution to a person or group that attempts to
acquire us without approval of our board of directors, and under certain
circumstances, the rights beneficially owned by the person or group may become
void. The plan also may have the effect of limiting shareholder participation in
certain transactions such as mergers or tender offers whether or not such
transactions are favored by incumbent directors and key management. In addition,
our executive officers may be more likely to retain their positions with us as a
result of the plan, even if their removal would be beneficial to shareholders
generally.

         Our articles of incorporation and our by-laws contain provisions,
including a staggered board provision, that make it more difficult for a third
party to gain control or acquire us without the consent of our board of
directors. These provisions also could discourage proxy contests and may make it
more difficult for dissident shareholders to elect representatives as directors
and take other corporate actions.

         These provisions of our governing documents may have the effect of
delaying, deferring or preventing a transaction or a change in control that
might be in the best interest of our shareholders.


                                       17



                                 USE OF PROCEEDS

         Our net proceeds from the sale of 1,000,000 shares of our common stock
in this offering are estimated to be approximately $ million after deducting the
underwriting discount and aggregate offering expenses payable by us. The
offering expenses are estimated to be approximately $225,000. If the
underwriters' over-allotment option is exercised in full, the net proceeds will
be approximately $ million.

         We intend to use the net proceeds of this offering to increase the
capital at our banks to pursue further growth and for general corporate
purposes.


                                       18



                                 CAPITALIZATION

         The following table sets forth our total indebtedness and
capitalization at June 30, 2003, on an historical basis and as adjusted for the
offering (assuming no exercise of the underwriters' over-allotment option) as if
such sale had been consummated on June 30, 2003. This data should be read in
conjunction with the consolidated financial statements and notes thereto
incorporated by reference into this prospectus from our Annual Report on Form
10-K for the fiscal year ended December 31, 2002, and from our Quarterly Report
on Form 10-Q for the quarter ended June 30, 2003.



                                                                                            JUNE 30, 2003
                                                                                       -------------------------
                                                                                          ACTUAL     AS ADJUSTED
                                                                                       -----------  -------------
                                                                                        (DOLLARS IN THOUSANDS)
                                                                                              

INDEBTEDNESS:
Other borrowings (including securities sold under agreement to repurchase,
   federal funds purchased and Federal Home Loan Bank advances).................        $197,439       $197,439
Notes payable under revolving credit line with an unaffiliated commercial bank..          26,000         26,000
Subordinated notes..............................................................          50,000         50,000
Long-term debt--trust preferred securities(1)....................................         76,816         76,816
                                                                                        --------       --------
   Total indebtedness...........................................................         350,255        350,255
                                                                                        --------       --------
SHAREHOLDERS' EQUITY:
Preferred stock, no par value; 20,000,000 shares authorized, of which 100,000
   shares are designated Junior Serial Preferred Stock A; no shares
   issued and outstanding.......................................................              --             --
Common stock, no par value; 30,000,000 shares authorized; 17,428,118 shares
   issued and outstanding; 18,428,118 shares issued and outstanding
   as adjusted(2)...............................................................          17,428         18,428
Surplus.........................................................................         158,597
Common stock warrants to acquire 263,886 shares(3)..............................           1,030          1,030
Retained earnings...............................................................          72,861         72,861
Accumulated other comprehensive loss............................................            (517)          (517)
                                                                                        --------       --------
   Total shareholders' equity...................................................         249,399
                                                                                        --------       --------
   Total capitalization.........................................................        $599,654       $
                                                                                        ========       ========
CAPITAL RATIOS:
Leverage ratio(4)...............................................................            7.5%               %
Tier 1 capital ratio............................................................            8.4
Total risk-based capital ratio..................................................           10.5

---------------------
(1)      Excludes $1.6 million of our long-term indebtedness related to the
         common securities of the capital trust subsidiaries we formed prior to
         2003. All of the common securities of these trust subsidiaries are held
         by Wintrust and are also eliminated on our consolidated balance sheet.
         Due to current interpretation of a recent change in required accounting
         treatment, in future periods we expect to reflect the common securities
         and the total amount of long-term debt on our balance sheet. This
         change will have no effect on our net interest income.
(2)      Does not include 2,913,775 shares subject to options and restricted
         stock unit awards outstanding at June 30, 2003, with a weighted
         average exercise price of $13.47.
(3)      The warrants have a weighted average exercise price of $14.65
         and expire between December 2003 and February 2013.
(4)      The leverage ratio is Tier 1 capital divided by average quarterly
         assets, after deducting intangible assets and net deferred tax assets
         in excess of regulatory maximum limits.



                                       19


                 PRICE RANGE OF COMMON STOCK AND DIVIDEND POLICY

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The following table sets forth the high and low sales prices
reported on the Nasdaq National Market for our common stock for the periods
indicated and the semi-annual dividends paid by us during such periods. The
following information gives effect to a 3-for-2 stock split effective as of
March 14, 2002.

                                     HIGH              LOW           DIVIDEND
                                     ----              ---           --------
2003
----
First Quarter....................... $33.65           $27.19           $0.0800
Second Quarter......................  32.40            27.74              --
Third Quarter (through September 2).  36.18            29.30           $0.0800

2002
----
First Quarter....................... $22.99           $18.33           $0.0600
Second Quarter......................  34.58            22.22              --
Third Quarter.......................  36.00            26.54           $0.0600
Fourth Quarter......................  32.66            25.45              --

2001
----
First Quarter....................... $12.75           $10.54           $0.0467
Second Quarter......................  17.62            11.67              --
Third Quarter.......................  21.41            16.27           $0.0467
Fourth Quarter......................  22.13            17.93              --

         As of September 2, 2003, there were approximately 1,880 shareholders of
record of our common stock.

COMMON STOCK DIVIDEND POLICY

         In January 2000, our board of directors approved the payment of our
first semi-annual cash dividend on our common stock. We have continued to pay a
semi-annual cash dividend since that time. The final determination of timing,
amount and payment of dividends on our common stock is at the discretion of our
board of directors and will depend upon our profitability, financial condition,
capital requirements and other relevant factors, including the restrictions
described below. Although we have increased the dividend rate every year since
we initiated payment of dividends, as a growing company we expect to continue to
retain at least 90% of our earnings to fund future growth and to build our
franchise.

         Because the principal source of our income at the holding company level
is dividends from our banks, our ability to pay dividends on common stock in the
future may be largely dependent on the banks' ability to pay dividends to us.
Any payment of dividends by the banks is subject to certain restrictions imposed
by federal and state banking laws and regulations. As a financial holding
company, our banks are now required to maintain capital sufficient to meet the
"well-capitalized" standards set by the regulators and will be able to pay
dividends to us only so long as their capital continues to exceed these levels.
Additionally, de novo banks are prohibited from paying dividends during the
first three years of operations.

         Our ability to pay cash dividends on our common stock is also subject
to statutory restrictions and restrictions arising under the terms of our
outstanding and any future debt securities and trust preferred securities. The
terms of such securities generally restrict payment of dividends on common stock
until required payments and distributions are made on those securities and may
impose additional restrictions in the future. Under applicable corporate law, we
are permitted to pay dividends only to the extent of our shareholders' equity.
Federal regulation of bank holding companies may also impose restrictions on the
ability of a bank holding company to pay dividends.


                                       20



                                  UNDERWRITING

         Subject to the terms and conditions set forth in the underwriting
agreement, the underwriters named below have severally agreed to purchase from
us an aggregate of 1,000,000 shares of common stock in the amount set forth
opposite their respective names.

                                                           NUMBER
                         UNDERWRITERS                    OF SHARES
         ----------------------------------------------- ---------
         RBC Dain Rauscher Inc..........................
         U.S. Bancorp Piper Jaffray Inc.................
         Raymond James & Associates, Inc................
         Stifel, Nicolaus & Company, Incorporated.......
         Sandler O'Neill & Partners, L.P................  ---------
            Total.......................................  1,000,000
                                                          =========

         The underwriting agreement provides that the underwriters' obligations
are subject to specified conditions precedent and that the underwriters are
committed to purchase all of the shares of our common stock offered hereby if
the underwriters purchase any of such shares of common stock.

         The underwriters have advised us that they propose to offer the shares
of common stock to the public at the public offering price set forth on the
cover page of this prospectus and to selected dealers at such price less a
concession not in excess of $ per share. The underwriters may allow and such
dealers may reallow a discount not in excess of $ per share to certain other
brokers and dealers. After the offering, the public offering price, concession,
discount and other selling terms may be changed by the underwriters.

         We have granted to the underwriters an option, exercisable for 30 days
after the date of this prospectus, to purchase up to 150,000 additional shares
of our common stock solely to cover over-allotments, if any, at the same price
per share to be paid by the underwriters for the other shares of common stock
offered hereby.

         The underwriters' commissions are shown in the following table. These
amounts are shown assuming both no exercise and full exercise of the
underwriters' option to purchase additional shares of common stock.

                                                             FULL
                                           NO EXERCISE     EXERCISE
                                           -----------     --------
         Per share........................ $               $
         Total............................ $               $


         In connection with the offering of the shares of our common stock, the
underwriters and any selling group members and their respective affiliates may
engage in transactions effected in accordance with Rule 104 of Regulation M
promulgated by the SEC that are intended to stabilize, maintain or otherwise
affect the market price of the shares of our common stock. Such transactions may
include over-allotment transactions in which an underwriter creates a short
position for its own account by selling more shares of our common stock than it
is committed to purchase from us. In such a case, to cover all or part of the
short position, the underwriters may purchase shares of our common stock in the
open market following completion of the initial offering of the shares of our
common stock. The underwriters also may engage in stabilizing transactions in
which they bid for, and purchase, shares of our common stock at a level above
that which might otherwise prevail in the open market for the purpose of
preventing or retarding a decline in the market price of the shares of our
common stock. The underwriters may also reclaim any selling concession allowed
to a dealer if the underwriters repurchase shares distributed by that dealer.
Any of the foregoing transactions may result in the maintenance of a price for
the shares of


                                       21


our common stock at a level above that which might otherwise prevail in the open
market. Neither we nor the underwriters makes any representation or prediction
as to the direction or magnitude of any effect that the transactions described
above may have on the price of the shares of our common stock. The underwriters
are not required to engage in any of the foregoing transactions and, if
commenced, such transactions may be discontinued at any time without notice.
These transactions may be effected on the Nasdaq National Market, in the
over-the-counter market or otherwise.

         In connection with this offering, some underwriters may also engage in
passive market making transactions in our common stock on the Nasdaq National
Market. Passive market making consists of displaying bids on the Nasdaq National
Market limited by the prices of independent market makers and effecting
purchases limited by those prices in response to order flow. Rule 103 of
Regulation M promulgated by the SEC limits the amount of net purchases that each
passive market maker may make and the displayed size of each bid. Passive market
making may stabilize the market price of our common stock at a level above that
which might otherwise prevail in the open market and, if commenced, may be
discontinued at any time.

         We agreed to indemnify the underwriters and their controlling persons
against specified liabilities, including liabilities under the Securities Act of
1933, or to contribute to payments the underwriters may be required to make in
respect thereof.

         We and our executive officers and directors have agreed that, except as
described in this prospectus, for a period of 90 days after the date of this
prospectus, we and they will not, without the prior written consent of RBC Dain
Rauscher Inc. on behalf of the underwriters, directly or indirectly, (1) offer,
pledge (except for pledges granted prior to the date of this prospectus), sell,
contract to sell, sell any option or contract to purchase, purchase any option
or contract to sell, grant any option, right or warrant to purchase, lend or
otherwise transfer or dispose of (subject to some exceptions) any shares of our
common stock, or any securities convertible into, or exercisable or exchangeable
for, our common stock or (2) enter into any swap or other agreement that
transfers, in whole or in part, any economic equivalent of ownership of shares
of our common stock.

         We have agreed that, except pursuant to a publicly announced stock
repurchase program to purchase shares of our common stock or under our stock
option plan or employee stock purchase plan, we will not for a period of 180
days after the date of this prospectus, without the prior written consent of RBC
Dain Rauscher Inc. on behalf of the underwriters, purchase, redeem or call for
redemption, or prepay or give notice of prepayment (or announce any redemption
or call for redemption, or any prepayment or notice of prepayment) of, any of
our securities.

         Certain representatives of the underwriters or their affiliates have
performed and may in the future perform investment banking and other financial
services for us and our affiliates for which they may receive advisory or
transaction fees, as applicable, plus out-of-pocket expenses, of the nature and
in amounts customary in the industry for these financial services. The
underwriters have informed us that they do not intend to confirm sales to any
discretionary account without the prior written approval of the customer in
compliance with NASD Rule 2720(l).


                                       22



                                 TRANSFER AGENT

         The transfer agent for our common stock is Illinois Stock Transfer
Company, 209 West Jackson Boulevard, Suite 903, Chicago, Illinois 60606.


                                  LEGAL MATTERS

         Certain legal matters relating to the common stock offered by this
prospectus have been passed upon for us by Vedder, Price, Kaufman & Kammholz,
P.C., Chicago, Illinois. Certain legal matters have been passed upon for the
underwriters by Jones Day, Chicago, Illinois.


                                     EXPERTS

         Ernst & Young LLP, independent auditors, have audited our consolidated
financial statements included in our Annual Report on Form 10-K for the year
ended December 31, 2002, as set forth in their report, which is incorporated by
reference in our Annual Report and in this prospectus. Our financial statements
are incorporated by reference in this prospectus in reliance on Ernst & Young
LLP's report, given on their authority as experts in accounting and auditing.


                       WHERE YOU CAN FIND MORE INFORMATION

         This prospectus is a part of a Registration Statement on Form S-3 that
we filed with the SEC under the Securities Act. This prospectus does not contain
all the information set forth in the registration statement, certain parts of
which are omitted in accordance with the rules and regulations of the SEC. For
further information with respect to us and the securities offered by this
prospectus, reference is made to the registration statement, including the
exhibits to the registration statement and the documents incorporated by
reference.

         We file annual, quarterly and special reports, proxy statements and
other information with the SEC. Our filings are available to the public over the
Internet at the SEC's web site at http://www.sec.gov. You may also read and copy
any document we file with the SEC at its public reference facilities at 450
Fifth Street, N.W., Washington, D.C. 20549. You can also obtain copies of the
documents at prescribed rates by writing to the Public Reference Section of the
SEC at 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at
1-800-SEC-0330 for further information on the operation of the public reference
facilities. Our SEC filings are also available on our web site at
http://www.wintrust.com, and at the office of the Nasdaq National Market. For
further information on obtaining copies of our public filings at the Nasdaq
National Market, you should call (212) 656-5060.

                       DOCUMENTS INCORPORATED BY REFERENCE

         We "incorporate by reference" into this prospectus the information we
file with the SEC, which means that we can disclose important information to you
by referring you to those documents. The information incorporated by reference
is an important part of this prospectus.

         Some information contained in this prospectus updates and supersedes
the information incorporated by reference and some information that we file
subsequently with the SEC will automatically update this prospectus. We
incorporate by reference the documents listed below:


                                       23


         o        our Annual Report on Form 10-K for the fiscal year ended
                  December 31, 2002, filed with the SEC on March 27, 2003 (File
                  No. 0-21923);

         o        our Quarterly Report on Form 10-Q for the quarter ended March
                  31, 2003, filed with the SEC on May 14, 2003 (File No.
                  0-21923);

         o        our Quarterly Report on Form 10-Q for the quarter ended June
                  30, 2003, filed with the SEC on August 14, 2003 (File No.
                  0-21923);

         o        our Current Report on Form 8-K filed with the SEC on January
                  16, 2003 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on February
                  4, 2003 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on April 18,
                  2003 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on April 24,
                  2003 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 30,
                  2003 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on July 17,
                  2003 (File No. 0-21923); and

         o        the descriptions of (a) our Common Stock contained in our
                  Registration Statement on Form 8-A dated January 3, 1997 (File
                  No. 0-21923), and (b) the associated preferred share purchase
                  rights contained in our Registration Statement on Form 8-A
                  dated August 28, 1998 (File No. 0-21923).

         We also incorporate by reference any filings we make with the SEC under
Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934 after
the initial filing of the registration statement that contains this prospectus
and before the time that all of the shares offered by this prospectus are sold.

         Any statement contained in a document incorporated by reference in this
prospectus shall be deemed to be modified or superseded for purposes of this
prospectus to the extent that a statement contained in this prospectus, or in
any other document filed later which is also incorporated in this prospectus by
reference, modifies or supersedes the statement. Any statement so modified or
superseded shall not be deemed to constitute a part of this prospectus except as
so modified or superseded. The information contained in this prospectus should
be read together with the information in the documents incorporated in this
prospectus by reference.

         You may request, either orally or in writing, and we will provide, a
copy of these filings at no cost by contacting David A. Dykstra, our Chief
Operating Officer, at the following address and phone number:

         Wintrust Financial Corporation
         727 North Bank Lane
         Lake Forest, Illinois 60045-1951
         (847) 615-4096



                                       24





                                1,000,000 SHARES




                         WINTRUST FINANCIAL CORPORATION



                                  COMMON STOCK




                          ---------------------------
                               PRICE $ PER SHARE
                          ---------------------------


RBC CAPITAL MARKETS
          U.S. BANCORP PIPER JAFFRAY
                              RAYMOND JAMES
                                     STIFEL, NICOLAUS & COMPANY
                                            INCORPORATED
                                                SANDLER O'NEILL & PARTNERS, L.P.




                            ------------------------
                                          , 2003
                            ------------------------






                                     PART II
                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

         The following table sets forth the various expenses payable in
connection with the sale and distribution of the securities being registered,
other than underwriting discounts and commissions. All of the amounts shown are
estimates, except for the SEC registration and NASD filing fees. We do not
expect our expenses in connection with this offering to exceed $225,000.

         SEC registration fee.....................     $    3,293
         NASD filing fee..........................          4,566
         Blue Sky and NASD qualifications fees....          5,000
         Accounting fees and expenses.............          5,000
         Legal fees and expenses..................        150,000
         Printing and mailing expenses............         25,000
         Miscellaneous............................         32,141
                                                       ----------
            Total.................................       $225,000
                                                         ========

ITEM 15.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         Insofar as indemnification for liabilities arising under the Securities
Act may be permitted to directors, officers, and controlling persons of Wintrust
pursuant to the following provisions, or otherwise, we have been advised that in
the opinion of the Securities and Exchange Commission such indemnification is
against public policy as expressed in the Securities Act and is, therefore,
unenforceable.

         In accordance with the Illinois Business Corporation Act (being Chapter
805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of the
Registrant's Certificate of Incorporation provide as follows:

         ARTICLE EIGHT: No director of the corporation shall be liable to the
corporation or its shareholders for monetary damages for breach of fiduciary
duty as a director except for liability (a) for any breach of the director's
duty of loyalty to the corporation or its shareholders, (b) for acts or
omissions not in good faith or that involve intentional misconduct of a knowing
violation of law, (c) under Section 8.65 of the BCA, as the same exists or
hereafter may be amended, or (d) for any transaction from which the director
derived an improper personal benefit.

         ARTICLE NINE, PARAGRAPH 1: The corporation shall indemnify, to the full
extent that it shall have power under applicable law to do so and in a manner
permitted by such law, any person made or threatened to be made a party to any
threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative, by reason of the fact that he or she
is or was a director, officer, employee or agent of the corporation, or who is
or was serving at the request of the corporation as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust or
other enterprise against liabilities and expenses reasonably incurred or paid by
such person in connection with such action, suit or proceeding. The corporation
may indemnify, to the full extent that it shall have power under applicable law
to do so and in a manner permitted by such law, any person made or threatened to
be made a party to any threatened, pending or completed action, suit or
proceeding, whether civil, criminal, administrative or investigative, by reason
of the fact that he or she is or was a director, officer, employee or agent of
the corporation, or is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise against liabilities and expenses reasonably
incurred or paid by such person in connection with such action, suit or

                                      II-1




proceeding. The words "liabilities" and "expenses" shall include, without
limitation: liabilities, losses, damages, judgments, fines, penalties, amounts
paid in settlement, expenses, attorneys' fees and costs. Expenses incurred in
defending a civil, criminal, administrative, investigative or other action, suit
or proceeding may be paid by the corporation in advance of the final disposition
of such action, suit or proceeding in accordance with the provisions of Section
8.75 of the BCA.

         The indemnification and advancement of expenses provided by this
Article shall not be deemed exclusive of any other rights to which any person
indemnified may be entitled under any statute, by-law, agreement, vote of
shareholders, or disinterested directors or otherwise, both as to action in his
official capacity and as to action in any other capacity while holding such
office, and shall continue as to a person who has ceased to be such director,
officer, employee or agent and shall inure to the benefit of the heirs,
executors and administrators of such person.

         PARAGRAPH 2: The corporation may purchase and maintain insurance on
behalf of any person referred to in the preceding paragraph against any
liability asserted against him or her and incurred by him or her in any such
capacity, or arising out of his or her status as such, whether or not the
corporation would have the power to indemnify him or her against such liability
under the provisions of this Article or otherwise.

         PARAGRAPH 3: For purposes of this Article, references to "the
corporation" shall include, in addition to the resulting corporation, any
constituent corporation (including any constituent of a constituent) absorbed in
a consolidation or merger which, if its separate existence had continued, would
have had power and authority to indemnify its directors, officers, employees or
agents, so that any person who is or was a director, officer, employee or agent
of such constituent corporation, or is or was serving at the request of such
constituent corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise, shall stand
in the same position under the provisions of this Article with respect to the
resulting or surviving corporation as he or she would have with respect to such
constituent corporation if its separate existence had continued.

         PARAGRAPH 4: The provisions of this Article shall be deemed to be a
contract between the corporation and each director or officer who serves in any
such capacity at any time while this Article and the relevant provisions of the
BCA, or other applicable law, if any, are in effect, and any repeal or
modification of any such law or of this Article shall not affect any rights or
obligations then existing with respect to any state of facts then or theretofore
existing or any action, suit or proceeding theretofore or thereafter brought or
threatened based in whole or in part upon any such state of facts.

         PARAGRAPH 5: For purposes of this Article, references to "other
enterprises" shall include employee benefit plans; references to "fines" shall
include any excise taxes assessed on a person with respect to any employee
benefit plan; and references to "serving at the request of the corporation"
shall include any service as a director, officer, employee or agent of the
corporation which imposes duties on, or involves services by, such director,
officer, employee or agent with respect to any employee benefit plan, its
participants, or beneficiaries; and a person who acted in good faith and in a
manner he or she reasonably believed to be in the interest of the participants
and beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner not opposed to the best interests of the corporation.

         Section 6.3 of the Registrant's By-laws provides as follows:

         SECTION 6.3. MANDATORY INDEMNIFICATION. To the extent that a director,
officer, employee or agent of a corporation, or any subsidiary or subsidiaries,
as the case may be, has been successful on the merits or otherwise in defense of
any action, suit or proceeding referred to in Sections 6.1 and 6.2, or in
defense of any claim, issue or matter therein, such person shall be indemnified


                                      II-2


against expenses (including attorneys' fees) actually and reasonably incurred by
him or her in connection therewith.

         The Illinois Business Corporation Act provides for indemnification of
officers, directors, employees and agents as follows:

         5/8.75 INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS;
INSURANCE. (a) A corporation may indemnify any person who was or is a party, or
is threatened to be made a party to any threatened, pending or completed action,
suit or proceeding, whether civil, criminal, administrative or investigative
(other than an action by or in the right of the corporation) by reason of the
fact that he or she is or was a director, officer, employee or agent of the
corporation, or who is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise, against expenses (including attorneys'
fees), judgments, fines and amounts paid in settlement actually and reasonably
incurred by such person in connection with such action, suit or proceeding, if
such person acted in good faith and in a manner he or she reasonably believed to
be in, or not opposed to the best interests of the corporation, and, with
respect to any criminal action or proceeding, had no reasonable cause to believe
his or her conduct was unlawful. The termination of any action, suit or
proceeding by judgment, order, settlement, conviction, or upon a plea of nolo
contendere or its equivalent, shall not, of itself, create a presumption that
the person did not act in good faith and in a manner which he or she reasonably
believed to be in or not opposed to the best interests of the corporation or,
with respect to any criminal action or proceeding, that the person had
reasonable cause to believe that his or her conduct was unlawful.

         (b)       A corporation may indemnify any person who was or is a party,
or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in
its favor by reason of the fact that such person is or was a director, officer,
employee or agent of the corporation, or is or was serving at the request of the
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees) actually and reasonably incurred by such person in
connection with the defense or settlement of such action or suit, if such person
acted in good faith and in a manner he or she reasonably believed to be in, or
not opposed to, the best interests of the corporation, provided that no
indemnification shall be made with respect to any claim, issue, or matter as to
which such person has been adjudged to have been liable to the corporation,
unless, and only to the extent that the court in which such action or suit was
brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, such person is
fairly and reasonably entitled to indemnity for such expenses as the court shall
deem proper.

         (c)      To the extent that a present or former director, officer or
employee of a corporation has been successful, on the merits or otherwise, in
the defense of any action, suit or proceeding referred to in subsections (a) and
(b), or in defense of any claim, issue or matter therein, such person shall be
indemnified against expenses (including attorneys' fees) actually and reasonably
incurred by such person in connection therewith if the person acted in good
faith and in a manner he or she reasonably believed to be in, or not opposed to,
the best interests of the corporation.

         (d)      Any indemnification under subsections (a) and (b) (unless
ordered by a court) shall be made by the corporation only as authorized in the
specific case, upon a determination that indemnification of the present or
former director, officer, employee or agent is proper in the circumstances
because he or she has met the applicable standard of conduct set forth in
subsections (a) or (b). Such determination shall be made with respect to a
person who is a director or officer at the time of the determination: (1) by the
majority vote of the directors who are not parties to such action, suit or
proceeding, even though less than a quorum, (2) by a committee of the directors
designated by a majority vote of the directors, even


                                      II-3



though less than a quorum, (3) if there are no such directors, or if the
directors so direct, by independent legal counsel in a written opinion, or (4)
by the shareholders.

         (e)     Expenses (including attorney's fees) incurred by an officer or
director in defending a civil or criminal action, suit or proceeding may be paid
by the corporation in advance of the final disposition of such action, suit or
proceeding upon receipt of an undertaking by or on behalf of the director or
officer to repay such amount if it shall ultimately be determined that such
person is not entitled to be indemnified by the corporation as authorized in
this Section. Such expenses (including attorneys' fees) incurred by former
directors and officers or other employees and agents may be so paid on such
terms and conditions, if any, as the corporation deems appropriate.

         (f)      The indemnification and advancement of expenses provided by or
granted under the other subsections of this Section shall not be deemed
exclusive of any other rights to which those seeking indemnification or
advancement of expenses may be entitled under any by-law, agreement, vote of
shareholders or disinterested directors, or otherwise, both as to action in his
or her official capacity and as to action in another capacity while holding such
office.

         (g)      A corporation may purchase and maintain insurance on behalf of
any person who is or was a director, officer, employee or agent of the
corporation, or who is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise, against any liability asserted against such
person and incurred by such person in any such capacity, or arising out of his
or her status as such, whether or not the corporation would have the power to
indemnify such person against such liability under the provisions of this
Section.

         (h)      If a corporation indemnifies or advances expenses to a
director or officer under subsection (b) of this Section, the corporation shall
report the indemnification or advance in writing to the shareholders with or
before the notice of the next shareholders meeting.

         (i)      For purposes of this Section, references to "the corporation"
shall include, in addition to the surviving corporation, any merging corporation
(including any corporation having merged with a merging corporation) absorbed in
a merger which, if its separate existence had continued, would have had the
power and authority to indemnify its directors, officers, and employees or
agents, so that any person who was a director, officer, employee or agent of
such merging corporation, or was serving at the request of such merging
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, shall stand in the same
position under the provisions of this Section with respect to the surviving
corporation as such person would have with respect to such merging corporation
if its separate existence had continued.

         (j)      For purposes of this Section, reference to "other enterprises"
shall include employee benefit plans; references to "fines" shall include any
excise taxes assessed on a person with respect to an employee benefit plan; and
references to "serving at the request of the corporation" shall include any
service as a director, officer, employee or agent of the corporation which
imposes duties on, or involves services by such director, officer, employee, or
agent with respect to an employee benefit plan, its participants, or
beneficiaries. A person who acted in good faith and in a manner he or she
reasonably believed to be in the best interests of the participants and
beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner "not opposed to the best interest of the corporation" as referred to in
this Section.

         (k)      The indemnification and advancement of expenses provided by or
granted under this Section shall, unless otherwise provided when authorized or
ratified, continue as to a person who has ceased to be a director, officer,
employee, or agent and shall inure to the benefit of the heirs, executors, and
administrators of that person.


                                      II-4



         (l)      The changes to this Section made by this amendatory Act of the
92nd General Assembly apply only to actions commenced on or after the effective
date of this amendatory Act of the 92nd General Assembly. (Last amended by P.A.
92-0033, L. '01, eff. 7-1-01.)

         Wintrust has purchased $30 million of insurance policies which insure
Wintrust's directors and officers against liability which they may incur as a
result of actions taken in such capacities. In addition, Wintrust maintains
fiduciary liability coverage up to a $5 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 16.  EXHIBITS

1.1      Form of Underwriting Agreement.*

2.1      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, WTFC Merger Co. and Advantage National Bancorp, Inc.
         dated July 2, 2003 (incorporated by reference to Annex A to the
         Company's proxy statement/prospectus included as part of its
         Registration Statement on Form S-4/A (No. 333-108099) filed with the
         Securities and Exchange Commission on September 2, 2003).

2.2      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, WTFC Merger Co. and Village Bancorp, Inc. dated August 7,
         2003 (incorporated by reference to Exhibit 2.2 to the Company's
         Registration Statement on Form S-4/A (No. 333-108099) filed with the
         Securities and Exchange Commission on September 2, 2003).

3.1      Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

3.2      Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

3.3      Amended and Restated By-laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q
         for the quarter ended March 31, 2003).

4.1      Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

4.2      Certain instruments defining the rights of holders of long-term debt of
         the Company and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         the Company and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. The Company hereby agrees to furnish a copy of any
         of these agreements to the Commission upon request.

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. regarding legality.*

23.1     Consent of Ernst & Young LLP.*

23.2     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in opinion
         filed as Exhibit 5.1).

24.1     Power of Attorney (set forth on signature page to this Registration
         Statement).


---------------------
*       Filed herewith.

ITEM 17.  UNDERTAKINGS

         (a)      We hereby undertake that for purposes of determining any
liability under the Securities Act of 1933, each filing of the registrant's
annual report pursuant to Section 13(a) or Section 15(d) of the Securities
Exchange Act of 1934 that is incorporated by reference in this registration
statement shall be deemed to be a new registration statement relating to the
securities offered herein, and the offering of such securities at that time
shall be deemed to be the initial bona fide offering thereof.


                                      II-5



         (b)      Insofar as indemnification for liabilities arising under the
Securities Act of 1933 may be permitted to directors, officers and controlling
persons of the registrant pursuant to the foregoing provisions, or otherwise,
the registrant has been advised that in the opinion of the Securities and
Exchange Commission such indemnification is against public policy as expressed
in the Act and is, therefore, unenforceable. In the event that a claim for
indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Act and will
be governed by the final adjudication of such issue.

         (c)      (1)      For purposes of determining any liability under the
Securities Act of 1933, the information omitted from the form of prospectus
filed as part of this registration statement in reliance upon Rule 430A and
contained in a form of prospectus filed by the registrant pursuant to Rule
424(b)(1) or (4) or 497(h) under the Securities Act shall be deemed to be part
of this registration statement as of the time it was declared effective.

                  (2)      For the purpose of determining any liability under
the Securities Act of 1933, each post-effective amendment that contains a form
of prospectus shall be deemed to be a new registration statement relating to the
securities offered therein, and the offering of such securities at that time
shall be deemed to be the initial bona fide offering thereof.


                                      II-6



                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, as amended,
the registrant certifies that it has reasonable grounds to believe that it meets
all of the requirements for filing on Form S-3 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Lake Forest, State of Illinois, on this 2nd day
of September, 2003.

                                     WINTRUST FINANCIAL CORPORATION

                                     By:  /s/ Edward J. Wehmer
                                          Edward J. Wehmer
                                          President and Chief Executive Officer

         We, the undersigned directors of Wintrust Financial Corporation, and
each of us, do hereby constitute and appoint each and any of Edward J. Wehmer
and David A. Dykstra, our true and lawful attorneys and agents, with full power
of substitution and resubstitution, to do any and all acts and things in our
name and behalf in any and all capacities and to execute any and all instruments
for us in our names in any and all capacities, which attorney and agent may deem
necessary or advisable to enable said corporation to comply with the Securities
Act of 1933, as amended, and any rules, regulations, and requirements of the
Securities and Exchange Commission, in connection with this Registration
Statement, including specifically, but without limitation, power and authority
to sign for us or any of us in our names in the capacities indicated below, any
and all amendments (including post-effective amendments) hereto and any other
registration statements related to the offering that is the subject of this
registration statement filed pursuant to Rule 462; and we do hereby ratify and
confirm all that said attorney and agent, or his substitute, shall do or cause
to be done by virtue thereof.

         Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons on the 2nd day
of September, 2003 in the capacities indicated.


                     SIGNATURE                              TITLE

             /s/ Edward J. Wehmer                  President, Chief Executive
         ------------------------------               Officer and Director
                 Edward J. Wehmer

              /s/ David L. Stoehr                 Executive Vice President and
         ------------------------------             Chief Financial Officer
                  David L. Stoehr                (Principal Accounting Officer)

              /s/ John S. Lillard                    Chairman and Director
         ------------------------------
                  John S. Lillard

                                                            Director
         ------------------------------
                  Peter D. Crist

             /s/ Bruce K. Crowther                          Director
         ------------------------------
                 Bruce K. Crowther

             /s/ Bert A. Getz, Jr.                          Director
         ------------------------------
                 Bert A. Getz, Jr.


                                      S-1


                     SIGNATURE                              TITLE

                                                            Director
         ------------------------------
                 Philip W. Hummer

             /s/ James B. McCarthy                          Director
         ------------------------------
                 James B. McCarthy

         /s/ Marguerite Savard McKenna
         ------------------------------                     Director
             Marguerite Savard McKenna

             /s/ Albin F. Moschner                          Director
         ------------------------------
                 Albin F. Moschner

              /s/ Thomas J. Neis                            Director
         ------------------------------
                  Thomas J. Neis

                                                            Director
         ------------------------------
               Hollis W. Rademacher

                                                            Director
         ------------------------------
               J. Christopher Reyes

             /s/ John J. Schornack                          Director
         ------------------------------
                 John J. Schornack

            /s/ Ingrid S. Stafford                          Director
         ------------------------------
                Ingrid S. Stafford


                                       S-2





                                  EXHIBIT INDEX

1.1      Form of Underwriting Agreement.*

2.1      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, WTFC Merger Co. and Advantage National Bancorp, Inc.
         dated July 2, 2003 (incorporated by reference to Annex A to the
         Company's proxy statement/prospectus included as part of its
         Registration Statement on Form S-4/A (No. 333-108099) filed with the
         Securities and Exchange Commission on September 2, 2003).

2.2      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, WTFC Merger Co. and Village Bancorp, Inc. dated August 7,
         2003 (incorporated by reference to Exhibit 2.2 to the Company's
         Registration Statement on Form S-4/A (No. 333-108099) filed with the
         Securities and Exchange Commission on September 2, 2003).

3.1      Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

3.2      Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

3.3      Amended and Restated By-laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q
         for the quarter ended March 31, 2003).

4.1      Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

4.2      Certain instruments defining the rights of holders of long-term debt of
         the Company and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         the Company and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. The Company hereby agrees to furnish a copy of any
         of these agreements to the Commission upon request.

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. regarding legality.*

23.1     Consent of Ernst & Young LLP.*

23.2     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in opinion
         filed as Exhibit 5.1).

24.1     Power of Attorney (set forth on signature page to this Registration
         Statement).


---------------------
*       Filed herewith.