Company: WTFCN
Filing Date: 2025-05-09
Form Type: 424B5
Source: 0001104659-25-046769
Chunk: 17

Company: WINTRUST FINANCIAL CORP
Filing Date: 2025-05-09
Form: 424B5
Chunk 17
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 in such circumstances. See “Description of Depositary Shares — Voting the Preferred Stock” on page S-30.

#### Preemptive and Conversion Rights
None.

#### Material U.S. Federal Income Tax Considerations
For a discussion of material United States federal income tax considerations of purchasing, owning and disposing of the depositary shares, see “Material U.S. Federal Income Tax Considerations.”

#### Listing
Prior to this offering, there has been no public market for the depositary shares. We intend to apply to list the depositary shares on The NASDAQ Global Select Market under the symbol “WTFCN.” If the application is approved, we expect trading of the depositary shares on The NASDAQ Global Select Market to begin within the 30-day period after the initial delivery of the depositary shares.

#### Use of Proceeds
We estimate that the net proceeds from this offering, after deducting the underwriting discounts and estimated offering expenses payable by us, will be approximately $414.7 million.

We intend to use the net proceeds from this offering for general corporate purposes, which may include the redemption of all or a portion of our outstanding shares of Series D preferred stock and/or Series E preferred stock and the corresponding depositary shares representing interests in the Series E preferred stock, subject to approval from the Federal Reserve. See “Use of Proceeds.”

#### Transfer Agent
Equiniti Trust Company, LLC will act as initial transfer agent for the Preferred Stock.

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#### Registrar and Depositary
U.S. Bank Trust Company, National Association will act as registrar and depositary.

#### Calculation Agent
Wintrust Investments, LLC, our subsidiary, will be the calculation agent for the Preferred Stock.

#### Risk Factors
Please refer to the section entitled “Risk Factors” beginning on page S-10and other information included or incorporated by reference in this prospectus supplement and the accompanying prospectus for a discussion of factors you should consider carefully before deciding to invest in the depositary shares.

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### RISK FACTORS
An investment in the depositary shares is subject to risks inherent to our business. Before making an investment decision, you should carefully consider the risks and uncertainties described below together with the risk factors and other information included in our Annual Report on Form 10-K for the year ended December 31, 2024, and in other documents that we subsequently file with the SEC, all of