WINTRUST FINANCIAL CORP
S-3/A, 1999-11-19
STATE COMMERCIAL BANKS
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    As filed with the Securities and Exchange Commission on November 19, 1999


                                                      Registration No. 333-90211


================================================================================
                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

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

                               AMENDMENT NO. 1 TO

                                    FORM S-3
                             REGISTRATION STATEMENT
                                      Under
                           The Securities Act of 1933

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

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

               Illinois                                36-3873352
     (State or Other Jurisdiction                    (IRS Employer
   of Incorporation or Organization)              Identification Number)

                              727 North Bank Lane
                        Lake Forest, Illinois 60045-1951
                                 (847) 615-4096
               (Address, Including Zip Code, and Telephone Number,
        Including Area Code, of Registrant's Principal Executive Offices)

                                David A. Dykstra
              Executive Vice President and Chief Financial 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.
                        Vedder, Price, Kaufman & Kammholz
                            222 North LaSalle Street
                          Chicago, Illinois 60601-1003
                                 (312) 609-7500

     Approximate date of commencement of proposed sale to the public: From time
to time, after this Registration Statement becomes effective.

     If the only securities being registered on this form are being offered
pursuant to dividend or interest reinvestment plans, please 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. [X]

     If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please 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. [ ]

     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 or until the Registration Statement shall become
effective on such date as the Commission, acting pursuant to said section 8(a),
may determine.


===============================================================================

<PAGE>

The information in this prospectus is not complete and may be changed. We may
not sell these securities until the registration statement filed with the
Securities and Exchange Commission is 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 NOVEMBER 19, 1999


PROSPECTUS

                         WINTRUST FINANCIAL CORPORATION

                         227,635 SHARES OF COMMON STOCK



     Certain shareholders of Wintrust Financial Corporation are offering for
sale from time to time up to 227,635 shares of our common stock under this
prospectus. The selling shareholders may offer the shares:

     o    to or through one or more underwriters,

     o    directly to purchasers,

     o    on the Nasdaq National Market in typical brokerage transactions,

     o    in negotiated transactions, or otherwise.

     The selling shareholders may sell the shares of common stock covered by
this prospectus:

     o    at market prices prevailing at the time of sale,

     o    at prices related to the then-prevailing market price, or

     o    at negotiated prices.



     Wintrust will not receive any proceeds from the sale of the shares of
common stock by the selling shareholders. No minimum purchase is required and no
arrangement has been made to have funds received by the selling shareholders
and/or any registered representatives placed in an escrow, trust or similar
account or arrangement.



     Wintrust's common stock is traded on the Nasdaq National Market under the
symbol "WTFC." On November 17, 1999, the closing price for the common stock as
reported on Nasdaq was $17.00 per share.


     YOU SHOULD CONSIDER, AMONG OTHER THINGS, THE INFORMATION SET FORTH IN "RISK
FACTORS" BEGINNING ON PAGE 6 OF THIS PROSPECTUS.

     THE SHARES OF COMMON STOCK THAT ARE BEING OFFERED ARE NOT SAVINGS ACCOUNTS
OR DEPOSITS OR OTHER OBLIGATIONS OF A BANK AND ARE NOT INSURED BY THE BANK
INSURANCE FUND OR THE FEDERAL DEPOSIT INSURANCE CORPORATION OR ANY GOVERNMENTAL
AGENCY.

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


                The date of this prospectus is November __, 1999


<PAGE>

                                TABLE OF CONTENTS

                                                                           Page
                                                                           ----

About This Prospectus........................................................2




Wintrust Financial Corporation -- Summary Information........................3




Risk Factors.................................................................6

Use of Proceeds.............................................................10

Selling Shareholders........................................................11

Plan of Distribution........................................................11

Transfer Agent..............................................................12

Legal Matters...............................................................13

Experts.....................................................................13


Where You Can Find More Information.........................................13






                              ABOUT THIS PROSPECTUS

     This prospectus is part of a registration statement that we filed with the
Securities and Exchange Commission; it provides you with a general description
of the securities offered. You should read this prospectus together with
additional information described under the heading "Where You Can Find More
Information."

                                        2

<PAGE>



                         WINTRUST FINANCIAL CORPORATION

     Wintrust Financial Corporation, an Illinois corporation, is a financial
services holding company headquartered in Lake Forest, Illinois, with total
assets of approximately $1.6 billion at September 30, 1999. Wintrust engages in
community banking and specialty finance businesses through its operating
subsidiaries: Lake Forest Bank and Trust Company; Hinsdale Bank and Trust
Company; North Shore Community Bank and Trust Company; Libertyville Bank and
Trust Company; Barrington Bank and Trust Company, N.A.; Crystal Lake Bank and
Trust Company, N.A.; First Insurance Funding Corporation (formerly First Premium
Services, Inc.), a commercial insurance premium finance company; Wintrust Asset
Management Company, N.A., a trust company subsidiary; and recently acquired
Tricom, Inc., which provides financial and administrative services to the
temporary staffing industry. In September 1996, each of the banking subsidiaries
then existing and First Insurance Funding, which were previously affiliated but
separately owned, became subsidiaries of Wintrust as a result of a transaction
which combined their respective holding companies under one parent company.


     Today, Wintrust provides community-oriented, personal and commercial
banking services primarily to individuals and small to mid-size businesses
through 24 banking facilities. The table below provides information regarding
each of our banks and their respective markets.



<TABLE>
<CAPTION>
                                                    TOTAL ASSETS            CHICAGO-AREA
                                                AT SEPTEMBER 30, 1999        COMMUNITIES         NUMBER
           BANK               DATE OPENED          (IN THOUSANDS)              SERVED        OF FACILITIES
- --------------------------  --------------      ---------------------    ------------------  -------------

<S>                         <C>                       <C>                <C>                        <C>
Lake Forest                 December 1991             $484,987           Lake Forest                5
                                                                         Lake Bluff                 1

Hinsdale                    October 1993               324,801           Hinsdale                   2
                                                                         Clarendon Hills(1)         1
                                                                         Western Springs(2)         1
                                                                         Burr Ridge                --

North Shore Community       September 1994             338,313           Wilmette                   3
                                                                         Kenilworth                --
                                                                         Glencoe                    2
                                                                         Winnetka                   1
                                                                         Skokie                     1

Libertyville                October 1995               215,519           Libertyville               3
                                                                         Mundelein                 --
                                                                         Vernon Hills              --

Barrington                  December 1996              159,977           Barrington                 1
                                                                         Barrington Hills          --
                                                                         Lake Barrington           --
                                                                         North Barrington          --
                                                                         South Barrington          --
                                                                         Inverness                 --

Crystal Lake                December 1997               83,402           Crystal Lake               3
                                                                         Cary                      --
</TABLE>
- ----------------
(1)  Operates in this community as Clarendon Hills Bank, a branch of Hinsdale
     Bank.
(2)  Operates in this community as Community Bank of Western Springs, a branch
     of Hinsdale Bank.

                                       3

<PAGE>


     Each of Wintrust's banking subsidiaries was founded as a de novo banking
organization (i.e., started new) within the last eight years. The organizational
efforts began in 1991, when a group of experienced bankers and local business
people identified an unfilled niche in the Chicago metropolitan area community
banking market. As large banks acquired smaller ones and personal service was
subjected to consolidation strategies, opportunities arose in affluent suburbs
for locally owned and operated banks emphasizing personal service. In pursuit of
this strategic opportunity, the group founded Lake Forest Bank in December 1991
to service the Lake Forest and Lake Bluff communities. Thereafter, as desirable
locations were procured in other attractive communities where management
successfully recruited locally known, experienced bank officers, our other banks
were organized with the participation of local residents and business leaders of
those communities.


     Through First Insurance Funding, Wintrust originates commercial insurance
premium finance loans on a national basis. Currently, the majority of these
loans are being purchased by our banks in order to fulfill the lending capacity
of the Banks. The loans originated by First Insurance Funding provide our banks
with attractive yielding assets as a supplement to their lending activities.
First Insurance Funding, which commenced operations approximately nine years
ago, is headquartered in Deerfield, Illinois. Based on limited industry data
available and First Insurance Funding management's experience in the industry,
management estimates that First Insurance Funding is one of the largest premium
finance companies operating in the United States. First Insurance Funding's loan
volume exceeded $600 million for the 12 months ended September 30, 1999. These
loans are originated by First Insurance Funding, working with medium and large
insurance agents and brokers throughout the United States. Insurance premiums
are financed primarily for commercial customers' purchases of liability,
property and casualty and other commercial insurance.

     Wintrust conducts trust operations through Wintrust Asset Management, a
separate subsidiary created on September 30, 1998, to expand Wintrust's trust
services in the communities served by our banks. Wintrust has experienced trust
personnel and offers trust services at Lake Forest Bank, North Shore Community
Bank, Hinsdale Bank, and Barrington Bank. Wintrust plans to offer on-site trust
services through Wintrust Asset Management at each of our remaining banks within
the next few years.

     The historical financial performance of Wintrust has been affected by the
high costs associated with growing market share in deposits and loans, opening
new banking facilities and building an experienced management team. Wintrust's
financial performance over the past five years reflects the improving financial
performance of our banks as they mature, adjusted for the significant costs of
opening new banks and branch offices. Wintrust's experience has been that it
generally takes from 13 to 24 months for new banking facilities to first achieve
operational profitability. Similarly, management currently expects a start-up
phase for Wintrust Asset Management of approximately two to three years before
the trust operations become profitable.

     In order to minimize the time lags typically experienced by de novo banks
in redeploying deposits into assets that provide attractive yields, since its
formation Wintrust has focused on the development of specialized earning asset
niches. Because management believes that our banks, like many community banks,
are not likely over time to generate loans to local customers for more than
about half of their respective lending capacities, it is anticipated that
Wintrust will continue to pursue specialized asset niches to allow Wintrust to
generate large volumes of homogenous assets that can be retained for investment,
or sold into the secondary market or securitized to generate fee income or for
liquidity management purposes.

     To date, Wintrust has identified and finances loans in several such asset
niches to enhance its loan-to-deposit ratio, including premium finance loans
originated by First Insurance Funding, indirect auto loans, mortgage warehouse
lending, medical and municipal funding, and, more recently,

                                       4

<PAGE>

homeowners and condominium association lending. On October 26, 1999, we added a
new earning asset and fee-based business niche through our acquisition of
Tricom, Inc., a financial and administrative service bureau to the temporary
staffing industry. Tricom, which is being operated as a subsidiary of Hinsdale
Bank, provides short-term accounts receivable financing and value-added,
out-sourced administrative services, such as data processing of payrolls,
billing and cash management services. Tricom's clients, located throughout the
United States, provide staffing services to businesses in diversified
industries. Based on third quarter 1999 volume, Tricom currently processes
payrolls with associated billings in excess of $200 million annualized.

     While committed to a continuing growth strategy, management's current focus
is to balance further asset growth with earnings growth. To this end, Wintrust
is seeking to more fully leverage the existing capacity of its operating
subsidiaries to support internal growth. Additionally, Wintrust is continuing to
pursue specialized earning-asset niches to shift the mix of earning assets to
higher-yielding loans. Wintrust is also focusing on controlling costs of funds
as the maturing Banks achieve more established customer bases.

     Wintrust's principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045, and its telephone number is (847) 615-4096.


                           FORWARD-LOOKING STATEMENTS

     Certain statements contained in or incorporated by reference into this
prospectus constitute forward-looking statements within the meaning of Section
27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act
of 1934. You can identify these statements from our use of the words "estimate,"
"project," "believe," "intend," "anticipate," "expect" and similar expressions.
These forward-looking statements may include, among other things:

     o    statements related to anticipated improvements in financial
          performance and management's long term performance goals,

     o    statements relating to Wintrust's business and growth strategies, and

     o    any other statements which are not historical facts.

     Such forward-looking statements involve known and unknown risks,
uncertainties and other important factors that could cause our actual results,
performance or achievements, or industry results, to differ materially from any
future results, performance or achievements expressed or implied by such
forward-looking statements. In addition, our past results of operations do not
necessarily indicate our future results. We discuss these and other
uncertainties in the "Risk Factors" section of this prospectus.


                                       5

<PAGE>

                                  RISK FACTORS

     Investing in our common stock involves risks. The discussion below
describes the most significant risk factors related to the offering. You should
carefully consider these risks and uncertainties before deciding to invest in
our common stock. If any of these risks or uncertainties actually occur, our
business could be adversely affected. In that event, the trading price of our
common stock could decline and you could lose all or a part of your investment.
This prospectus and the information incorporated into it by reference also
contain forward-looking statements that involve risks and uncertainties. Our
actual results could differ materially from those anticipated in the forward-
looking statements as a result of certain factors, including those described
below and elsewhere in the documents incorporated by reference in this
prospectus.

DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY; OUR HISTORICAL
EARNINGS WERE ENHANCED THROUGH THE RECOGNITION OF PRIOR YEARS' NET TAX OPERATING
LOSSES.

     Wintrust's historical results have been impacted by its strategy of de novo
bank formations and branch openings through which Wintrust has built an
infrastructure that management believes can support additional internal growth
in our banks' respective markets. To expand into additional communities in and
around Chicago, Wintrust may undertake additional de novo bank formations or
branch openings. Based on Wintrust's experience, management believes that it
generally takes from 13 to 24 months for new banking facilities to first achieve
operational profitability, due to 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. Wintrust's two newest subsidiaries, Crystal Lake Bank,
which opened in December 1997, and Wintrust Asset Management, which we formed in
late 1998, are not yet operating profitably.

     The level of reported net income, return on average equity and return on
average assets for Wintrust will in the near term continue to be impacted by
start-up costs associated with our de novo bank and branching operations and the
start-up of Wintrust Asset Management. To the extent Wintrust undertakes
additional branching and de novo bank and business formations, Wintrust is
likely to continue to experience the effects of higher operating expenses
relative to operating income from the new operations. This may limit increases
in profitability, although management currently intends to focus on balancing
future growth with earnings improvements and anticipates that future results of
operations will reflect greater leveraging of the investments Wintrust has made
to date in the infrastructures of the existing banks.

     In addition, unlike prior periods, our reported net income in 1999 and
future periods will not benefit significantly from recognition of net operating
loss carryforwards. The value of prior NOL's recognized for financial statement
reporting purposes during 1998 was $3.4 million and in 1997 was $4.2 million.

WE MAY NOT BE ABLE TO SUCCESSFULLY IMPLEMENT OUR ACQUISITION STRATEGY.

     Although Wintrust has historically grown through de novo bank formations
and the establishment of new branch offices, Wintrust's strategic plan also
includes potential acquisition of other financial institutions in attractive
markets and potential acquisitions of specialty finance or commercial finance
businesses that offer unique earning asset niches. Growth through acquisition
may offer Wintrust the opportunity to increase market share in existing and new
markets without incurring the full earnings impact of start-up operations.
However, there can be no assurance that potential acquisitions will be available
on terms acceptable or favorable to Wintrust or that the required regulatory
approvals for any proposed acquisitions will be obtained. There also can be no
assurance that Wintrust will be able

                                       6

<PAGE>

to successfully integrate, operate and manage any business that it acquires so
as to maintain or increase profitability.

     During October 1999, Wintrust completed a part cash, part stock acquisition
of 10-year old, Milwaukee-based Tricom, Inc., a financial and administrative
service bureau to the temporary staffing industry. The transaction is consistent
with our stated strategy of adding a variety of diversified earning asset and
fee-based business niches to augment our community-based banking revenues. While
we entered into employment agreements ranging from one to three years with four
senior officers of Tricom and expect the acquisition to be accretive to earnings
per share during the first full year of operations, Wintrust management has no
direct experience managing or financing this type of business, and we could
encounter unanticipated difficulties. Accordingly, there can be no assurance
that we will succeed in increasing our profitability as a result of the
acquisition.

WE DEPEND ON OUR SENIOR MANAGEMENT.

     Wintrust's success to date has been influenced strongly by its ability to
attract and to retain senior management experienced in banking and financial
services. Wintrust's ability to retain its executive officers and the current
management teams of each of our banks, First Insurance Funding and Wintrust
Asset Management, and, as Wintrust grows, to attract and retain qualified
additional senior and middle management, will continue to be important to
successful implementation of Wintrust's strategies. Wintrust does not currently
maintain key-man life insurance policies. 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 Wintrust's business and
financial results.

     Wintrust has entered into employment agreements with Edward J. Wehmer, who
has served as Wintrust's president since inception and, since May 1998, as chief
executive officer, and with its other senior management and the senior officers
of its subsidiaries. The agreements provide for, among other things, certain
non-competition agreements, severance arrangements and benefits.

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

     Wintrust's allowance for possible loan losses is established in
consultation with management of its operating subsidiaries and is maintained at
a level considered adequate by management to absorb loan losses that are
inherent in the portfolio. The amount of future losses is susceptible to changes
in economic, operating and other conditions, including changes in interest
rates, that may be beyond Wintrust's 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 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 possible loan
losses is adequate to absorb losses on any existing loans that may become
uncollectible, there can be no assurance that the allowance for possible loan
losses will prove sufficient to cover actual loan losses in the future.

     A portion of Wintrust's assets are comprised of insurance premium finance
loans that Wintrust generates through First Insurance Funding. These loans,
intended to enhance the average yield of earning assets of the banks, may
involve a different level of risk of collection than generally associated with
loan portfolios of more traditional community banks.

                                       7

<PAGE>

WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

     Our earnings are derived from the operations of our subsidiaries, and we
are principally dependent on net interest income, calculated as the difference
between interest earned on loans and investments and the interest expense paid
on deposits and other borrowings. Like other banks and financial institutions,
Wintrust's 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 the economic environment may
influence the growth rate of loans and deposits, the quality of the loan
portfolio and loan and deposit pricing. While management has 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. If market interest rates should move contrary
to our "gap" position on interest earning assets and interest bearing
liabilities, the "gap" will work against us and our net interest income may be
negatively affected. Measured as of September 30, 1999, our short-term gap
position was relatively neutral in that the level of our interest-sensitive
assets that reprice within one year approximately matched the level of our
liabilities that reprice within the same period when adjusted for the effect of
interest rate cap contracts that we have entered into. Measured as of the same
date, we were slightly asset sensitive for the one- to five-year time frame.
While this would suggest that we would generally benefit from rising interest
rates, there can be no assurance that a dramatic change in the interest rate
environment will not adversely affect our results.

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 Wintrust
encounters strong direct competition for deposits, loans and other financial
services in all of its market areas. Wintrust's principal competitors include
other commercial banks, savings banks, savings and loan associations, mutual
funds, money market funds, finance companies, trust companies, insurers, leasing
companies, credit unions, mortgage companies, private issuers of debt
obligations and suppliers of other investment alternatives, such as securities
firms. Many of Wintrust's non-bank competitors are not subject to the same
degree of regulation as that imposed on bank holding companies, federally
insured banks and national or Illinois chartered banks. As a result, such
non-bank competitors have advantages over Wintrust in providing certain
services. In addition, in recent years, several major multi-bank holding
companies have entered or expanded in the Chicago metropolitan market.
Generally, these financial institutions are significantly larger than Wintrust
and have greater access to capital and other resources. In addition, 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.

REGULATORY RESTRICTIONS ON DIVIDEND PAYMENTS FROM THE BANKS MAY AFFECT OUR
ABILITY TO COMMENCE PAYING DIVIDENDS TO OUR SHAREHOLDERS.

     Wintrust has never paid a dividend to shareholders. As a holding company,
our ability to commence payment of dividends in the future will be largely
dependent on receipt of dividend income from our subsidiaries. In 1998, Lake
Forest Bank paid cash dividends to Wintrust in the amount of $8.25 million. None
of Wintrust's other banking subsidiaries has paid any dividends to date. Under
the provisions of the Illinois Banking Act, dividends may not be declared by
Lake Forest Bank, Hinsdale Bank, North Shore Community Bank, nor Libertyville
Bank except out of each bank's net profits (as defined therein), and unless each
bank has transferred to surplus at least one-tenth of its net profits since the
date of the declaration of the last preceding dividend, until the amount of its
surplus is at least equal to its capital. However, as Federal Reserve member
banks, dividends declared in any calendar year by any of the banks may not
exceed its net profit for the year plus its retained net profits for the
preceding two years. In addition, each of Barrington Bank and Crystal Lake Bank
is currently subject to additional

                                       8

<PAGE>

restrictions prohibiting the payment of dividends by a de novo bank in its first
three years of operations. The de novo period will end for Barrington Bank in
December 1999, and for Crystal Lake Bank in December 2000. Subsequent to these
dates, the banks would be allowed to pay dividends subject to the regulatory
limitations that are applicable to national banks. As of September 30, 1999,
based upon applicable regulatory limitations, our bank subsidiaries (other than
Barrington Bank and Crystal Lake) had the capacity to pay approximately $13.1
million as dividends to Wintrust, subject to regulatory capital maintenance
requirements.

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

     Wintrust, our banks and our trust company subsidiary are subject to
extensive federal and state legislation, regulation and supervision. Recently
enacted, proposed and future legislation and regulations have had, will continue
to have or may have significant impact on the financial services industry. Some
of the legislative and regulatory changes may benefit Wintrust, the banks and
Wintrust Asset Management; others, however, may increase our costs of doing
business and thus advantage our competitors.

OUR BUSINESS MAY BE NEGATIVELY IMPACTED BY THE YEAR 2000 ISSUE.

     A critical issue has emerged in the banking industry, and generally for all
industries that are heavily reliant upon computers, regarding how existing
software application programs and operating systems can accommodate the date
value for the Year 2000. The Year 2000 issue is the result of computer programs
being written using two digits (rather than four) to define the applicable year.
As such, certain programs that have time-sensitive software may recognize a date
using "00" as the Year 1900 rather than the Year 2000. As a result, the year
1999 (i.e. "99") could be the maximum date value these systems will be able to
accurately process. During 1997, management began the process of working with
its outside data processor and other software vendors to ensure that Wintrust is
prepared for the Year 2000. That process continued during 1998 and was completed
in mid-1999. Regardless of the Year 2000 compliance of Wintrust's systems, there
can be no assurance that Wintrust will not be adversely affected by the failure
of others to become Year 2000 compliant. Such risks may include potential losses
related to loans made to third parties whose businesses are adversely affected
by the Year 2000 issue, the disruption or inaccuracy of data provided by
non-Year 2000 compliant third parties and possible business disruption caused by
the failure of service providers, such as security and data processing companies
or power or telecommunications utilities, to become Year 2000 compliant. Because
of these uncertainties, there can be no assurance that the Year 2000 issue will
not have a material financial impact in any future period, although management
does not anticipate a material adverse effect.

THE FUTURE SALES OF OUR COMMON STOCK OR OTHER SECURITIES MAY DILUTE THE VALUE OF
THE COMMON STOCK.

     The board of directors has the authority, without action or vote of the
shareholders, to issue all or part of any authorized but unissued shares of
common stock, including shares authorized but unissued under Wintrust's stock
option plans. In the future, we may need to issue additional securities, through
public or private offerings, in order to raise additional capital to support our
growth. Any such issuance will dilute the percentage of ownership interest of
shareholders and may dilute the per share book value of the common stock. In
addition, option holders may exercise their options at a time when we would
otherwise be able to obtain additional equity capital on more favorable terms.

     The sale, or availability for sale, of a substantial number of shares of
common stock in the public market as a result of or following this offering
could adversely affect the common stock's market and could impair our ability to
raise additional capital through the sale of equity securities.

                                       9

<PAGE>

                                 USE OF PROCEEDS

     The selling shareholders will not pay any of the proceeds from the sale of
the shares of common stock to Wintrust. We expect to incur expenses in
connection with this offering in the amount of approximately $22,500.00 for
registration, legal, accounting and miscellaneous fees and expenses. We will not
pay for expenses such as commissions and discounts of brokers, dealers or agents
or the fees and expenses of counsel, if any, for the selling shareholders. See
"Selling Shareholders" and "Plan of Distribution."


                              SELLING SHAREHOLDERS

     This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 227,635 shares of common
stock. Wintrust newly issued all of these shares to the selling shareholders in
October 1999 in payment of part of the purchase price of our acquisition of
Tricom. Because the issuance of the shares in that transaction was not
registered with the SEC, the selling shareholders have "restricted stock."

     We are registering the shares to enable the selling shareholders to resell
the shares in the public market from time to time or on a delayed basis and to
permit secondary trading of the shares after they are sold by the selling
shareholders. We are paying for the registration of such securities but will not
pay for the fees and expenses of the selling shareholders, their attorneys or
other representatives, as a result of the sale of such securities by the selling
shareholders. See "Use of Proceeds" and "Plan of Distribution."

     The following table sets forth, to the best of our knowledge, information
concerning the selling shareholders, the number of shares to be offered and sold
by the selling shareholders and the amount of common stock that will be owned by
the selling shareholders following the offering (assuming sale of all shares of
common stock being offered hereby) by the selling shareholders.

<TABLE>
                                OWNERSHIP OF      NUMBER OF SHARES       OWNERSHIP OF       PERCENTAGE OF
                                COMMON STOCK       OF COMMON STOCK       COMMON STOCK       COMMON STOCK
SELLING STOCKHOLDER           PRIOR TO OFFERING     TO BE OFFERED       AFTER OFFERING   OWNED AFTER OFFERING
- -------------------           -----------------  -------------------  ----------------- ----------------------
<S>                                <C>                 <C>                    <C>                <C>
John Leopold(1)..............      188,442             188,442                0                  --
Mark Kahn....................       39,193              39,193                0                  --
</TABLE>
- ----------------
(1)  Mr. Leopold, the president of Tricom, Inc., a recently acquired subsidiary
     of Hinsdale Bank, entered into an employment agreement with the Company to
     continue to serve in this position for a period of one year, commencing on
     the date of acquisition. In addition, pursuant to the terms of the
     acquisition agreement, Mr. Leopold has a conditional right to a Wintrust
     board seat if Mr. Leopold continues to own more than 94,221 shares of
     Wintrust on December 31, 1999.


                              PLAN OF DISTRIBUTION

     The common stock offered by this prospectus may be offered and sold from
time to time by the selling shareholders. As used herein, "selling shareholders"
includes those individuals or entities who may have had shares of common stock
given to them as a gift by a named selling stockholder after the date of this
prospectus and any individuals or entities who may have shares of common stock
pledged to them as collateral by a named selling stockholder after the date of
this prospectus. See "Selling Shareholders." The shares of common stock covered
by this prospectus may be sold by the selling

                                       10

<PAGE>

shareholders in one or more types of transactions (which may include block
transactions) on Nasdaq, in the over-the-counter market, in negotiated
transactions, through put or call options transactions relating to the shares of
common stock, through short sales of shares of common stock, or a combination of
such methods of sale, or otherwise at prices and at terms then prevailing or at
prices related to the then current market price, or in negotiated transactions.
The shares of common stock may be sold by one or more of the following methods:
(a) a block trade in which the broker or dealer so engaged will attempt to sell
the shares of common stock as agent but may position and resell a portion of the
block as principal in order to facilitate the transaction; (b) a purchase by a
broker or dealer as principal, and the resale by such broker or dealer for its
account pursuant to this prospectus, including resale to another broker or
dealer; or (c) ordinary brokerage transactions and transactions in which the
broker solicits purchasers. Thus, the period of distribution of these shares of
common stock may occur over an extended period of time. This offering is
expected to terminate on October 26, 2000, or such earlier date on which all
shares offered have been sold.

     The selling shareholders may effect such transactions by selling the shares
of common stock directly to purchasers or to or through a broker or dealer, who
may act as an agent or principal. Such broker or dealer may receive compensation
in the form of discounts, concessions, or commissions from the selling
shareholders and/or the purchasers of shares of common stock for whom such
broker or dealer may act as agent or to whom he sells as principal, or both
(which compensation as to a particular broker or dealer might be in excess of
customary commissions). We know of no existing arrangements between any selling
stockholder, broker, dealer, underwriter or agent relating to the sale or
distribution of the shares of common stock.

     The selling shareholders will not pay any of the proceeds from the sale of
the shares of common stock to us. We expect to incur expenses in connection with
this offering in the amount of approximately $22,500 for registration, legal,
accounting and miscellaneous fees and expenses. The selling shareholders will be
solely responsible for commissions and discounts of brokers, dealers or agents,
other selling expenses and the fees and expenses of their own counsel, if any,
none of which will be borne by the company.

     In offering the securities, the selling shareholders and any broker-dealers
and any other participating broker-dealers who execute sales for the selling
shareholders may be deemed to be "underwriters" within the meaning of Section
2(11) of the Securities Act in connection with such sales, and any profits
realized by the selling shareholders and the compensation of such broker-dealers
may be deemed to be underwriting discounts and commissions. In addition, any
shares covered by this prospectus which qualify for sale pursuant to Rule 144
may be sold under Rule 144 rather than pursuant to this prospectus.

     We intend to advise the selling shareholders that while they are selling
the securities, they (1) are required to comply with Regulation M under the
Securities Exchange Act of 1934 (as described in more detail below), (2) may not
engage in any stabilization activity, except as permitted under the Exchange
Act, (3) are required to furnish each broker-dealer (who may offer this common
stock) copies of this prospectus, and (4) may not bid for or purchase any
securities of Wintrust or attempt to induce any person to purchase any
securities except as permitted under the Exchange Act.

     Regulation M under the Exchange Act prohibits, with certain exceptions,
participants in a distribution from bidding for or purchasing, for an account in
which the participant has a beneficial interest, any of the securities that are
the subject of the distribution. Regulation M also governs bids and purchases
made in order to stabilize the price of a security in connection with a
distribution of the security.

                                       11

<PAGE>

                                 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,
222 North LaSalle Street, Chicago, Illinois 60601-1003. A member of such firm
serves as a non-voting member of the board of directors of Hinsdale Bank.


                                     EXPERTS

     The consolidated financial statements of Wintrust and its subsidiaries
incorporated in this prospectus by reference to Wintrust's Annual Report on Form
10-K for the year ended December 31, 1998, have been audited by KPMG LLP,
independent certified public accountants, as stated in their report. Their
report has been incorporated herein by reference in reliance on the authority of
said firm as experts in auditing and accounting.

                                       12

<PAGE>


                       WHERE YOU CAN FIND MORE INFORMATION

     We file reports, proxy statements and other information with the SEC, as
required. You may copy and inspect the reports, proxy statements and other
information at the public reference facilities maintained by the SEC at 450
Fifth Street, N.W., Washington, D.C. 20549, or at the SEC's Regional Offices at
7 World Trade Center, New York, New York 10048, or at 500 West Madison Street,
Chicago, Illinois 60661. The Public Reference Section of the SEC at 450 Fifth
Street, N.W., Washington, D.C. 20549 may also provide, at prescribed rates,
copies of such material. The SEC also maintains a Web site that contains
reports, proxy and information statements and other information regarding
registrants, including Wintrust, that file electronically with the SEC. The
address of the site is http://www.sec.gov. You may also inspect reports and
other information concerning Wintrust at the National Association of Securities
Dealers, Inc., 1735 K Street, N.W., Washington, D.C. 20006. The reports that
Wintrust files with the SEC are also available on our Web site
(http://www.wintrust.com).

     The SEC allows us to "incorporate by reference" the information we file
with it, 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, and information that we file later with
the SEC will automatically update and supersede this information. We incorporate
by reference the documents listed below and any future filings made with the SEC
under Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934
until this offering terminates:

     (1) Our Annual Report on Form 10-K for the fiscal year ended December 31,
1998.

     (2) Our Quarterly Report on Form 10-Q for the quarter ended March 31, 1999.

     (3) Our Quarterly Report on Form 10-Q for the quarter ended June 30, 1999.

     (4) Our Quarterly Report on Form 10-Q for the quarter ended September 30,
1999.

     (5) Our Current Reports on Form 8-K dated April 29, 1999, September 17,
1999, October 19, 1999, and October 26, 1999.

     (6) The descriptions of (a) our Common Stock contained in our Registration
Statement on Form 8-A dated January 3, 1997, and (b) the associated preferred
share purchase rights contained in our Registration Statement on Form 8-A dated
August 28, 1998.

     You can request copies of these filings at no cost by contacting David A.
Dykstra, Executive Vice President, in writing at Wintrust Financial Corporation,
727 North Bank Lane, Lake Forest, Illinois 60045-1951, or by phone at (847)
615-4096.

     You should rely only on the information incorporated by reference or
provided in this prospectus. We have not authorized anyone else to provide you
with different information. We are not making an offer of these securities in
any state where the offer is not permitted. You should not assume that the
information in this prospectus is accurate as of any date other than the date on
the front of this prospectus.


                                       13

<PAGE>

                 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 fee. We do not expect our expenses in connection
with this offering to exceed $22,500.00.


          SEC registration fee....................   $ 1,079.76
          Accounting fees and expenses............     7,500.00
          Legal fees and expenses.................    10,000.00
          Miscellaneous...........................     3,920.24
                                                     ----------
               Total..............................   $22,500.00
                                                     ==========


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
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

                                      II-1

<PAGE>

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.

     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,

                                      II-2

<PAGE>

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 director, officer, employee or agent 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.

     (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 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 (1) by the Board of Directors by a majority vote of a quorum
consisting of directors who were not parties to such action, suit or proceeding,
or (2) if such a quorum is not obtainable, or, even if obtainable, if a quorum
of disinterested directors so directs, by independent legal counsel in a written
opinion, or (3) by the shareholders.

     (e)  Expenses incurred 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, officer, employee or agent to repay such amount if it shall
ultimately be determined that he or she is not entitled to be indemnified by the
corporation as authorized in this Section.

     (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.

                                      II-3

<PAGE>

     (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 has paid indemnity or has advanced expenses to a
director, officer, employee or agent, 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. (Last amended by P.A. 88-43, L. '93, eff. 1-1-94.)

     Wintrust has purchased $20 million of insurance policies which insures
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 $2 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 16.  EXHIBITS

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).

                                      II-4

<PAGE>

3.3    Amended By-laws of Wintrust Financial Corporation (incorporated by
       reference to Exhibit 3(i) of the Company's Form 10-Q for the quarter
       ended June 30, 1998).

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    Preferred Securities Guarantee Agreement by and between Wintrust
       Financial Corporation and Wilmington Trust Company dated September 29,
       1998, relating to the 9.00% Cumulative Trust Preferred Securities of
       Wintrust Capital Trust I (incorporated by reference to Exhibit 4.2 of the
       Company's Form 10-K for the year ended December 31, 1998).

4.3    Indenture by and between Wintrust Financial Corporation and Wilmington
       Trust Company dated September 29, 1998, relating to the 9.00%
       Subordinated Debentures issued to Wintrust Capital Trust I (incorporated
       by reference to Exhibit 4.3 of the Company's Form 10-K for the year ended
       December 31, 1998).

4.4    Amended and Restated Trust Agreement by and among Wintrust Financial
       Corporation, Wilmington Trust Company and the Administrative Trustees
       named therein dated September 29, 1998, relating to the 9.00% Cumulative
       Trust Preferred Securities of Wintrust Capital Trust I (incorporated by
       reference to Exhibit 4.4 of the Company's Form 10-K for the year ended
       December 31, 1998).

4.5    Form of Preferred Security Certificate of Wintrust Capital Trust I
       (incorporated by reference to Exhibit 4.5 of the Company's Form 10-K for
       the year ended December 31, 1998) (included as an exhibit to Exhibit
       4.4).

4.6    Form of Subordinated Debenture (incorporated by reference to Exhibit 4.6
       of the Company's Form 10-K for the year ended December 31, 1998)
       (included as an exhibit to Exhibit 4.3).


5.1   Opinion of Vedder, Price, Kaufman & Kammholz re: legality.


*23.1  Consent of KPMG LLP.

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

24     Power of Attorney (included on signature page of registration statement).
- ----------------
*    filed herewith.

ITEM 17.  UNDERTAKINGS

          (a)  We hereby undertake:

               (1)  To file, during any period in which offers or sales are
being made, a post-effective amendment to this registration statement:

                    (i)  to include any prospectus required by Section 10(a)(3)
     of the Securities Act of 1933;

                                      II-5

<PAGE>

                    (ii) to reflect in the prospectus any facts or events
     arising after the effective date of the registration statement (or the most
     recent post-effective amendment thereof) which, individually or in the
     aggregate, represent a fundamental change in the information set forth in
     the registration statement. Notwithstanding the foregoing, any increase or
     decrease in volume of securities offered (if the total dollar value of
     securities offered would not exceed that which was registered) and any
     deviation from the low or high end of the estimated maximum offering range
     may be reflected in the form of prospectus filed with the Commission
     pursuant to Rule 424(b) if, in the aggregate, the changes in volume and
     price represent no more than a 20 percent change in the maximum aggregate
     offering price set forth in the "Calculation of Registration Fee" table in
     the effective registration statement; and

                    (iii) to include any material information with respect to
     the plan of distribution not previously disclosed in the registration
     statement or any material change to such information in the registration
     statement;

     PROVIDED, HOWEVER, that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if
the information required to be included in a post-effective amendment by those
paragraphs is contained in periodic reports filed with or furnished to the
Commission by the registrant pursuant to Section 13 or 15(d) of the Securities
Exchange Act of 1934 that are incorporated by reference in the registration
statement.

          (2)  That, for the purpose of determining any liability under the
Securities Act of 1933, each such post-effective amendment 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; and

          (3)  To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the
termination of the offering.

     (b)  The undersigned registrant hereby undertakes 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.

     (c)  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.

                                      II-6

<PAGE>

                                   SIGNATURES


     Pursuant to the requirements of the Securities Act of 1933, 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 Amendment No. 1 to
the Registration Statement to be signed on its behalf by the undersigned,
thereunto duly authorized, in the City of Lake Forest, State of Illinois on
November 19, 1999.


                                        WINTRUST FINANCIAL CORPORATION

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




     Pursuant to the requirements of the Securities Act of 1933, this Amendment
No. 1 to the registration statement has been signed by the following persons in
the capacities and on the date indicated.


             Name                          Title                     Date
             ----                          -----                     ----


/s/ EDWARD J. WEHMER
- -----------------------------  President and Chief Executive   November 19, 1999
Edward J. Wehmer                    Officer and Director

/s/ DAVID A. DYKSTRA            Executive Vice President and
- -----------------------------      Chief Financial Officer     November 19, 1999
David A. Dykstra                (Principal Financial Officer)

/s/ TODD A. GUSTAFSON*
- -----------------------------      Vice President-Finance      November 19, 1999
Todd A. Gustafson              (Principal Accounting Officer)

/s/ JOHN S. LILLARD*
- -----------------------------       Chairman and Director      November 19, 1999
John S. Lillard

/s/ JOSEPH ALAIMO*
- -----------------------------             Director             November 19, 1999
Joseph Alaimo

/s/ PETER CRIST*
- -----------------------------             Director             November 19, 1999
Peter Crist


- -----------------------------             Director             November 19, 1999
Bruce K. Crowther

/s/ MAURICE F. DUNNE, JR.*
- -----------------------------             Director             November 19, 1999
Maurice F. Dunne, Jr.

/s/ WILLIAM C. GRAFT*
- -----------------------------             Director             November 19, 1999
William C. Graft


- -----------------------------             Director             November 19, 1999
Kathleen R. Horne

/s/ JAMES E. MAHONEY*
- -----------------------------             Director             November 19, 1999
James E. Mahoney

/s/ JAMES B. MCCARTHY*
- -----------------------------             Director             November 19, 1999
James B. McCarthy


                                      II-7

<PAGE>

             Name                          Title                     Date
             ----                          -----                     ----


/s/ MARGUERITE SAVARD MCKENNA*
- -----------------------------             Director             November 19, 1999
Marguerite Savard McKenna

/s/ ALBIN F. MOSCHNER*
- -----------------------------             Director             November 19, 1999
Albin F. Moschner

/s/ THOMAS J. NEIS*
- -----------------------------             Director             November 19, 1999
Thomas J. Neis

/s/ HOLLIS W. RADEMACHER*
- -----------------------------             Director             November 19, 1999
Hollis W. Rademacher

/s/ J. CHRISTOPHER REYES*
- -----------------------------             Director             November 19, 1999
J. Christopher Reyes


- -----------------------------             Director             November 19, 1999
Peter Rusin

/s/ JOHN N. SCHAPER*
- -----------------------------             Director             November 19, 1999
John N. Schaper

/s/ JOHN J. SCHORNACK*
- -----------------------------             Director             November 19, 1999
John J. Schornack

/s/ INGRID S. STAFFORD*
- -----------------------------             Director             November 19, 1999
Ingrid S. Stafford

/s/ JANE R. STEIN*
- -----------------------------             Director             November 19, 1999
Jane R. Stein

/s/ KATHARINE V. SYLVESTER*
- -----------------------------             Director             November 19, 1999
Katharine V. Sylvester

/s/ LEMUEL H. TATE, JR.*
- -----------------------------             Director             November 19, 1999
Lemuel H. Tate, Jr.


- -----------------------------             Director             November 19, 1999
Larry Wright


*By:/s/ DAVID A. DYKSTRA
    -------------------------
     David A. Dykstra
     Attorney-in-Fact


                                      II-8

<PAGE>

                                  EXHIBIT LIST


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 By-laws of Wintrust Financial Corporation (incorporated by
       reference to Exhibit 3(i) of the Company's Form 10-Q for the quarter
       ended June 30, 1998).

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    Preferred Securities Guarantee Agreement by and between Wintrust
       Financial Corporation and Wilmington Trust Company dated September 29,
       1998, relating to the 9.00% Cumulative Trust Preferred Securities of
       Wintrust Capital Trust I (incorporated by reference to Exhibit 4.2 of the
       Company's Form 10-K for the year ended December 31, 1998).

4.3    Indenture by and between Wintrust Financial Corporation and Wilmington
       Trust Company dated September 29, 1998, relating to the 9.00%
       Subordinated Debentures issued to Wintrust Capital Trust I (incorporated
       by reference to Exhibit 4.3 of the Company's Form 10-K for the year ended
       December 31, 1998).

4.4    Amended and Restated Trust Agreement by and among Wintrust Financial
       Corporation, Wilmington Trust Company and the Administrative Trustees
       named therein dated September 29, 1998, relating to the 9.00% Cumulative
       Trust Preferred Securities of Wintrust Capital Trust I (incorporated by
       reference to Exhibit 4.4 of the Company's Form 10-K for the year ended
       December 31, 1998).

4.5    Form of Preferred Security Certificate of Wintrust Capital Trust I
       (incorporated by reference to Exhibit 4.5 of the Company's Form 10-K for
       the year ended December 31, 1998) (included as an exhibit to Exhibit
       4.4).

4.6    Form of Subordinated Debenture (incorporated by reference to Exhibit 4.6
       of the Company's Form 10-K for the year ended December 31, 1998)
       (included as an exhibit to Exhibit 4.3).


5.1   Opinion of Vedder, Price, Kaufman & Kammholz re: legality.


*23.1  Consent of KPMG LLP.

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

24     Power of Attorney (included on signature page of registration statement).
- ----------------
*    filed herewith.




                                                                   Exhibit 23.1



The Board of Directors
Wintrust Financial Corporation:

We consent to the use of our report incorporated herein by reference and to the
reference to our firm under the heading "Experts" in Amendment No. 1 to the
Registration Statement (No. 333-90211) on Form S-3.


                                                     KPMG LLP


Chicago, Illinois
November 18, 1999



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