As filed with the Securities and Exchange Commission on October 26, 2004
                                                      Registration No. 333-_____
================================================================================

                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                   ___________

                                    FORM S-8
                             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                               (I.R.S. Employer
of Incorporation or Organization)                            Identification No.)

                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
    (Address, including zip code, of registrant's principal executive office)

                           __________________________

                              TOWN BANKSHARES, LTD.
                            1997 STOCK INCENTIVE PLAN
                            (Full title of the plan)

                                   ___________

                                DAVID A. DYKSTRA
                         SENIOR EXECUTIVE VICE PRESIDENT
                           AND CHIEF OPERATING OFFICER
                         WINTRUST FINANCIAL CORPORATION
                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
                                 (847) 615-4096
 (Name, address and telephone number, including area code, of agent for service)

                                   Copies to:
                              JOHN R. OBIALA, ESQ.
                     VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.
                            222 NORTH LASALLE STREET
                             CHICAGO, ILLINOIS 60601
                                 (312) 609-7500

                                   ___________



                                                    CALCULATION OF REGISTRATION FEE
====================================================================================================================================
             TITLE OF SECURITIES                 AMOUNT TO        PROPOSED MAXIMUM          PROPOSED MAXIMUM           AMOUNT OF
              TO BE REGISTERED                 BE REGISTERED  OFFERING PRICE PER SHARE  AGGREGATE OFFERING PRICE   REGISTRATION FEE
------------------------------------------------------------------------------------------------------------------------------------
                                                                                                                
Common Stock, no par value per share*(1)(2)        94,177           $25.00(3)                   $2,354,425              $299(3)
====================================================================================================================================

*        Including the preferred share purchase rights associated therewith.
(1)      Together with an indeterminate number of additional shares which may be
         necessary to adjust the number of shares offered pursuant to the plan
         as a result of a stock split, stock dividend or similar adjustment of
         the outstanding Common Stock pursuant to Rule 416(a).
(2)      Reflects shares of Common Stock that may be issued pursuant to the Town
         Bankshares, Ltd. 1997 Stock Incentive Plan.
(3)      Pursuant to Rule 457(h)(1) under the Securities Act of 1933, as
         amended, the proposed maximum offering price per share and the
         registration fee have been estimated based on the weighted average
         exercise price of $25 for 94,177 shares of Common Stock covered by
         options outstanding under the plan as of October 25, 2004.





            INTRODUCTORY STATEMENT NOT FORMING PART OF THE PROSPECTUS

         This Registration Statement registers 94,177 shares of common stock of
Wintrust Financial Corporation ("Wintrust") that may be issued upon exercise of
outstanding stock options previously granted by Town Bankshares, Ltd., a
Wisconsin corporation ("Town Bankshares"), under the Town Bankshares, Ltd. 1997
Stock Incentive Plan (the "Plan"). Effective October 15, 2004, Wintrust acquired
Town Bankshares through a merger of Town Bankshares with and into Wintrust (the
"Merger"). In connection with the Merger, each outstanding share of Town
Bankshares common stock was converted into the right to receive 1.283 shares of
Wintrust common stock and $58.10 in cash. At the effective time of the Merger,
previously granted options to purchase Town Bankshares common stock then
outstanding under the Plan became exercisable for shares of Wintrust common
stock in accordance with the terms of the Merger and the Plan. Each outstanding
and unexercised stock option to purchase shares of Town Bankshares common stock
is deemed to constitute an option to acquire, on the same terms and conditions
as were applicable under the original option prior to the Merger, the number of
shares of Wintrust common stock equal to the product, rounded down to the
nearest whole share, of the number of shares of Town Bankshares common stock
subject to the original option and 2.297, at a price per share equal to the
exercise price per share of the Town Bankshares common stock under the original
option divided by 2.297, rounded up, if necessary, to the nearest cent.

                                       2


                                     PART I

              INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS

         The documents containing information required by this section, which
relate to the shares of common stock of Wintrust Financial Corporation being
registered and remaining available for issuance pursuant to the exercise of
outstanding stock options previously granted by Town Bankshares, Ltd. under the
Town Bankshares, Ltd. 1997 Stock Incentive Plan, will be given to those persons
who hold outstanding options to purchase Town Bankshares common stock granted
under the Town Bankshares, Ltd. 1997 Stock Incentive Plan, all of whom were
employees or directors of Town Bankshares or its affiliates immediately prior to
the Merger. Such documents are not required to be filed with the Commission as a
part of this Registration Statement or as exhibits.

                                       3


                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

         The following documents filed with the Securities and Exchange
Commission (the "SEC") by Wintrust Financial Corporation, an Illinois
corporation ("Registrant"), are incorporated in this Registration Statement by
reference:

         o        Annual Report on Form 10-K for the year ended December 31,
                  2003, filed with the SEC on March 15, 2004 (File No. 0-21923);

         o        Proxy Statement in connection with the Registrant's 2004
                  annual meeting of shareholders;

         o        Quarterly Report on Form 10-Q for the quarter ended March 31,
                  2004, filed with the SEC on May 10, 2004 (File No. 0-21923);

         o        Quarterly Report on Form 10-Q for the quarter ended June 30,
                  2004, filed with the SEC on August 9, 2004 (File No. 0-21923);

         o        Current Report on Form 8-K filed with the SEC on January 21,
                  2004 (File No. 0-21923);

         o        Current Report on Form 8-K filed with the SEC on April 20,
                  2004 (File No. 0-21923);

         o        Current Report on Form 8-K filed with the SEC on May 11, 2004
                  (File No. 0-21923);

         o        Current Report on Form 8-K filed with the SEC on July 20, 2004
                  (File No. 0-21923);

         o        Current Report on Form 8-K filed with the SEC on September 30,
                  2004 (File No. 0-21923);

         o        Current Reports on Form 8-K filed with the SEC on October 15,
                  2004 (File Nos. 0-21923); and

         o        the description of (a) the Registrant's common stock contained
                  in its Registration Statement on Form 8-A dated January 3,
                  1997 (File No. 0-21923), and (b) the associated preferred
                  share purchase rights contained in the Registrant's
                  Registration Statement on Form 8-A dated August 28, 1998 (File
                  No. 0-21923).

         All documents subsequently filed by Registrant pursuant to Sections
13(a), 13(c), 14 and 15(d) of the Securities Exchange Act of 1934, as amended,
prior to the filing of a post-effective amendment which indicates that all
securities offered hereby have been sold or which deregisters all securities
then remaining unsold shall be deemed incorporated by reference in this
Registration Statement and shall be deemed a part hereof from the date of filing
of such documents. Any statement contained in a document incorporated or deemed
to be incorporated by reference herein shall be deemed to be modified or
superseded for purposes of this Registration Statement to the extent that a
statement contained herein or in any other subsequently filed document which
also is or is deemed to be incorporated by reference herein modifies or
supersedes such statement. Any such statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of this
Registration Statement.

                                       4



ITEM 4.  DESCRIPTION OF SECURITIES.

         Not applicable.

ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL.

         Not applicable.

ITEM 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         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 Articles 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 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 

                                       5



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
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. 

                                       6



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 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.

                                       7


         (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.

         (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.)

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

ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED.

         Not applicable.

                                       8


ITEM 8.  EXHIBITS.

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

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

         4.3      Amended and Restated By-Laws of Wintrust Financial Corporation
                  (incorporated by reference to Exhibit 3.3 of the Registrant's
                  Quarterly Report on Form 10-Q for the quarter ended March 31,
                  2003).

         4.4      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
                  Registrant's Form 8-A Registration Statement filed with the
                  SEC on August 28, 1998).

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

         23.1     Consent of Ernst & Young LLP.

         24.1     Powers of Attorney (included on the signature pages of the
                  Registration Statement).

         99.1     Town Bankshares, Ltd. 1997 Stock Incentive Plan, as amended.

         99.2     Form of Option Conversion Agreement.

ITEM 9.  UNDERTAKINGS.

         (a) The undersigned registrant hereby undertakes:

                  (1) To file, during any period in which offers or sales are
         being made, a post-effective amendment to this Registration Statement
         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 set forth 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.

                  (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 (and, where applicable, each filing of the
Plan's annual report pursuant to 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 

                                       9


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 policy as expressed in the Act and will be
governed by the final adjudication of such issue.

                                       10


                                   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 the requirements for filing on Form S-8 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 26th day
of October, 2004.

                                    WINTRUST FINANCIAL CORPORATION

                                    By:/s/ David A. Dykstra
                                       _________________________________________
                                       David A. Dykstra
                                       Senior Executive Vice President and Chief
                                       Operating Officer


         We, the undersigned officers and 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 attorney and agent,
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 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, as amended,
this 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, Chief Executive
----------------------------        Officer and Director        October 26, 2004
Edward J. Wehmer

/s/ David L. Stoehr             Executive Vice President and
----------------------------       Chief Financial Officer
David L. Stoehr                 (Principal Accounting Officer)  October 26, 2004

/s/ John S. Lillard                 Chairman and Director       October 26, 2004
----------------------------
John S. Lillard

/s/ Peter D. Crist                         Director             October 26, 2004
----------------------------
Peter D. Crist

/s/ Bruce K. Crowther                      Director             October 26, 2004
----------------------------
Bruce K. Crowther

/s/ Bert A. Getz, Jr.                      Director             October 26, 2004
----------------------------
Bert A. Getz, Jr.

                                       11


            NAME                           TITLE                     DATE
            ----                           -----                     ----

/s/ Philip W. Hummer                       Director             October 26, 2004
----------------------------
Philip W. Hummer
                                       
-----------------------------              Director
Paul J. Liska
                                       

/s/ James B. McCarthy                      Director             October 26, 2004
-----------------------------
James B. McCarthy
                                       
-----------------------------              Director
Albin F. Moschner

/s/ Thomas J. Neis                         Director             October 26, 2004
----------------------------
Thomas J. Neis

/s/ Hollis W. Rademacher                   Director             October 26, 2004
----------------------------
Hollis W. Rademacher
                                       
/s/ J. Christopher Reyes                                        October 26, 2004
-----------------------------              Director
J. Christopher Reyes

/s/ John J. Schornack                      Director             October 26, 2004
-----------------------------
John J. Schornack
                                       
/s/ Ingrid S. Stafford                     Director             October 26, 2004
-----------------------------
Ingrid S. Stafford

                                       12


                                INDEX TO EXHIBITS

EXHIBIT
 NUMBER                         DESCRIPTION OF EXHIBIT
 ------                         ----------------------

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

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

4.3      Amended and Restated By-Laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Registrant's Quarterly
         Report on Form 10-Q for the quarter ended March 31, 2003).

4.4      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 Registrant's Form 8-A
         Registration Statement filed with the SEC on August 28, 1998).

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

23.1     Consent of Ernst & Young LLP.

24.1     Powers of Attorney (included on the signature pages of the Registration
         Statement).

99.1     Town Bankshares, Ltd. 1997 Stock Incentive Plan.

99.2     Form of Option Conversion Agreement.