Federal Home Loan Bank of Chicago

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers. On September 15, 2026, James H. Hegenbarth was declared director-elect to serve as a member director of the Board of Directors (the “Board”) of the Federal Home Loan Bank of Chicago (the “Bank”). Mr. Hegenbarth is the President and a Director of Bank CMG in Madison, Wisconsin and was declared elected to serve a four-year term beginning January 1, 2027 and ending December 31, 2030. This directorship is being filled without an election because the number of nominees for member director for the state of Wisconsin is equal to the number of open directorships, which is one. Mr. Hegenbarth was declared director-elect to the Board in accordance with the rules governing the election of Federal Home Loan Bank member directors specified in the Federal Home Loan Bank Act (“Bank Act”) and the related regulations of the Federal Housing Finance Agency (“FHFA”). For more information on these rules, see “Item 10. Directors, Executive Officers and Corporate Governance” starting on page 77 in the Bank’s 2025 Annual Report on Form 10-K, filed with the Securities and Exchange Commission on March 10, 2026 (the “2025 Form 10-K”). The Board has not yet determined on which committees Mr. Hegenbarth will serve beginning in 2027. All directors serving on the Bank’s Board for 2027 are expected to receive compensation under the Bank’s 2027 Board of Directors Compensation Policy, which has not yet been approved by the Board. All directors are also entitled to participate in a non-qualified, unfunded, deferred compensation plan, under which each Bank director has the opportunity to defer all or a portion of their compensation. Pursuant to the Bank Act and FHFA regulations, the Bank’s member directors are required to be an officer or director of a member of the Bank. The Bank is a cooperative, and conducts its advances business, the Mortgage Partnership Finance Program, and letters of credit almost exclusively with its members. Therefore, in the normal course of business, the Bank extends credit to members whose officers or directors may serve as Bank directors. The Bank extends credit to these members on market terms that are no more favorable than the terms of comparable transactions with other members who are not considered related parties. Additionally, the Bank’s community investment activities may involve a member with an officer or director who is a Bank director, or another entity with an officer or director who serves as Bank director. These transactions are conducted in the ordinary course of business of the Bank’s business and are subject to the same eligibility and other program criteria and requirements as all other comparable transactions the Bank enters into. For further discussion, see “Related Persons and Related Transactions” on page 109 of the Bank’s 2025 Form 10-K. Signature(s) Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. Federal Home Loan Bank of Chicago By: /s/ Laura M. Turnquest Name: Laura M. Turnquest Date: September 15, 2026 Title: Executive Vice President, Chief Legal Officer, General Counsel, and Corporate Secretary