WINTRUST FINANCIAL CORP

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, DC 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

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Filed by a Party other than the Registrant ☐

Check the appropriate box:

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Preliminary Proxy Statement

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Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

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Definitive Proxy Statement

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Definitive Additional Materials

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Soliciting Material under § 240.14a-12

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Wintrust Financial Corporation

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(Name of Registrant as Specified in its Charter)

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(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

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No fee required.

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Fee paid previously with preliminary materials.

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Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

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WINTRUST FINANCIAL CORPORATION

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

TO BE HELD ON MAY 28, 2026

To the Shareholders of Wintrust Financial Corporation:

You are cordially invited to attend the 2026 Annual Meeting of Shareholders (the “Annual Meeting”) of Wintrust Financial Corporation (the “Company”) to be held at our offices located at 9700 West Higgins Road, 2nd Floor, Rosemont, Illinois 60018 on Thursday, May 28, 2026, at 9:00 a.m. Central Time, for the following purposes:

To elect the 12 nominees for director named in this Proxy Statement to hold office until the 2027 Annual Meeting of Shareholders or until a successor has been elected and qualified;

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To approve, on an advisory (non-binding) basis, the Company’s executive compensation as described in this Proxy Statement;

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To ratify the appointment of Ernst & Young LLP to serve as the independent registered public accounting firm for fiscal year 2026; and

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To transact such other business as may properly come before the meeting and any adjournment thereof.

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The record date for determining shareholders entitled to notice of, and to vote at, the Annual Meeting was the close of business on March 30, 2026. We encourage you to attend the Annual Meeting. Whether or not you plan to attend the Annual Meeting, prompt voting will be appreciated.

Two of our current directors, William J. Doyle and H. Patrick Hackett, Jr., are not standing for re-election this year. Messrs. Doyle and Hackett have been valued members of the Board of Directors (the “Board”) since 2017 and 2008, respectively, and we ask that you join the Board in thanking them for their time and service to the Company and in thanking Mr. Hackett for his leadership of the Board as non-executive Chairman over the past nine years.

By order of the Board of Directors,

Kathleen M. Boege

Corporate Secretary

April 9, 2026

WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL MEETING, IT IS IMPORTANT THAT YOU VOTE BY ONE OF THE METHODS NOTED IN THE ATTACHED PROXY STATEMENT.

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting of Shareholders to be Held on May 28, 2026: This Notice of the Annual Meeting, Proxy Statement and the 2025 Annual Report on Form 10-K are Available at: https://materials.proxyvote.com/97650W.