Exhibit 8.1

VEDDER PRICE                          VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.
                                      222 NORTH LASALLE STREET
                                      CHICAGO, ILLINOIS 60601
                                      312-609-7500
                                      FACSIMILE: 312-609-5005

                                      OFFICES IN CHICAGO, NEW YORK CITY
                                      AND LIVINGSTON, NEW JERSEY



                                      October 24, 2003



Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois  60045

     Re:  Registration Statement on Form S-4
          ----------------------------------

Ladies and Gentlemen:

         We have acted as counsel to Wintrust Financial Corporation, an Illinois
corporation ("Wintrust"), in connection with the proposed merger (the "Merger")
of WTFC Merger Co., a Delaware corporation and wholly-owned subsidiary of
Wintrust ("WTFC"), with and into Village Bancorp, Inc., a Delaware corporation
("Village"), pursuant to the terms of that certain Agreement and Plan of Merger
dated as of August 7, 2003, by and among Wintrust, WTFC and Village (the
"Agreement"), as described in the Registration Statement on Form S-4, filed by
Wintrust with the Securities and Exchange Commission (the "Commission") on
October 24, 2003 (the "Registration Statement"), under the Securities Act of
1933, as amended (the "Act"). This opinion is being rendered pursuant to the
requirements of Form S-4 under the Act.

         In rendering this opinion, we have examined originals or copies,
certified or otherwise identified to our satisfaction, of (i) the Agreement,
(ii) the Registration Statement and (iii) such other documents, certificates and
records as we have deemed necessary or appropriate for purposes of rendering the
opinion set forth herein. As to any facts material to the opinion set forth
herein which were not independently established or verified, we have relied upon
factual statements and representations of officers and other representatives of
Wintrust and others. We have also assumed that, in rendering this opinion, the
Merger will be consummated pursuant to Delaware law strictly in accordance with
the terms of the Agreement.

         Based upon and subject to the foregoing, in our opinion, the discussion
contained in the proxy statement/prospectus included as part of the Registration
Statement under the heading "DESCRIPTION OF THE MERGER -- Tax consequences of
the merger" constitutes, in all material respects, a fair and accurate summary
of the United States federal income tax consequences of the Merger to the
parties described therein.

         This opinion is based on the Internal Revenue Code of 1986, as amended,
the Income Tax Regulations promulgated by the Treasury Department thereunder and
judicial authority reported as of the date hereof. We have also considered the
position of the Internal Revenue Service (the






Wintrust Financial Corporation
October 24, 2003
Page 2


"Service") reflected in published and private rulings as of the date hereof.
Although we are not aware of any pending changes to these authorities that would
alter our opinion, there can be no assurances that future legislation or
administrative changes, court decisions or Service interpretations will not
significantly modify the opinion expressed herein, possibly with retroactive
effect.

         Although the discussion under the heading "DESCRIPTION OF THE MERGER --
Tax consequences of the merger" in the proxy statement/prospectus is based on
our interpretation of existing sources of law and expresses what we believe a
court would properly conclude if presented with the same issues, no assurances
can be given that such interpretations would be followed if they were to become
the subject of judicial or administrative proceedings.

         We hereby consent to the use of this opinion in connection with said
Registration Statement and to the use of our name under the heading "DESCRIPTION
OF THE MERGER -- Tax consequences of the merger" in the proxy
statement/prospectus included therein. In giving this consent, we do not hereby
concede that we are within the category of persons whose consent is required
under Section 7 of the Act or the rules and regulations of the Commission
promulgated thereunder. This opinion is expressed as of the date hereof and
applies only to the disclosures set forth in the proxy statement/prospectus and
Registration Statement. We disclaim any undertaking to advise you of any
subsequent changes of the facts stated or assumed herein or any subsequent
changes in applicable law.

                                     Very truly yours,




                                     /s/ VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.