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

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

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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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NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

TO BE HELD ON MAY 22, 2025

To the Shareholders of Wintrust Financial Corporation:

You are cordially invited to attend the 2025 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 22, 2025, at 9:00 a.m. Central Time, for the following purposes:

To elect the 13 nominees for director named in this Proxy Statement to hold office until the 2026 Annual Meeting of Shareholders or until a successor has been elected and qualified;

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To consider a proposal to approve the Company’s 2025 Stock Incentive Plan;

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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 2025; 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 24, 2025. We encourage you to attend the Annual Meeting. Whether or not you plan to attend the Annual Meeting, prompt voting will be appreciated.

Scott K. Heitmann is not standing for re-election this year due to the Company’s policy that a director retire at the Annual Meeting following his or her 76th birthday. Edward J. Wehmer, Founder and Senior Advisor of the Company, also is not standing for re-election this year, but he will continue to serve as Founder and Senior Advisor. Messrs. Heitmann and Wehmer have been valued members of the Board of Directors (the “Board”) since 2008 and since inception in 1996, respectively, and we ask that you join the Board in thanking Messrs. Heitmann and Wehmer for their time and service as members of the Board.

By order of the Board of Directors,

Kathleen M. Boege

Corporate Secretary

April 3, 2025

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 22, 2025: This Notice of the Annual Meeting, Proxy Statement and the 2024 Annual Report on Form 10-K are Available at: https://materials.proxyvote.com/97650W.