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. The Board of Directors (“Board”) of the Federal Home Loan Bank of Chicago (the “Bank”) is comprised of member directors and independent directors who are elected by the Bank’s members in accordance with the rules governing the election of Federal Home Loan Bank directors specified in the Federal Home Loan Bank Act (“Bank Act”) and the related regulations of the Federal Housing Finance Agency (“FHFA”), as discussed under Item 10 - Directors, Executive Officers, and Corporate Governance on page 77 of the Bank’s 2025 Annual Report on Form 10-K filed with the Securities and Exchange Commission on March 10, 2026 (“2025 Form 10-K”). On October 26, 2026, the Bank announced that the following directors have been elected to its Board as member directors:\ 1. Betsy A. Johnson, Chairman and Chief Executive Officer of Solutions Bank, Forreston, Illinois was re-elected to serve a four-year term on the Board beginning January 1, 2027 and ending December 31, 2030; and 2. James H. Hegenbarth, President and Director of Bank CMG, Madison, Wisconsin was elected to serve a four-year term on the Board beginning January 1, 2027 and ending December 31, 2030. With respect to the election of Mr. Hegenbarth, the Bank issued a Current Report on Form 8-K on September 15, 2026 (after the nomination period closed) announcing that Mr. Hegenbarth was the only member director nominee for the state of Wisconsin and had been declared director-elect to the Board in accordance with the rules governing the election of Federal Home Loan Bank member directors. In addition, on October 26, 2026, the Bank announced that the following director has been elected to its Board as a public interest independent director: 1. Kevin L. Newell, Founder and CEO of Royal Capital Group, Milwaukee, Wisconsin was re-elected to serve a four-year term on the Board as a public interest independent director beginning January 1, 2027 and ending December 31, 2030. The Board has not yet determined on which committees each of the directors elected 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 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.

Item 5.07 Submission of Matters to a Vote of Security Holders. On October 23, 2026, the Bank declared the voting results for its 2026 election of member and independent directors, which the Bank announced as described in Item 5.02 of this Current Report on Form 8-K (this “Form 8-K”). Complete voting results are included in the Bank’s Letter to Members dated October 26, 2026, attached as Exhibit 99.1 to this Form 8-K.

Item 7.01 Regulation FD Disclosure. Attached as Exhibit 99.1 to this Form 8-K is a copy of the Bank’s Letter to Members dated October 26, 2026, regarding the results of the 2026 election for member and independent directors. The information being furnished pursuant to Item 7.01 on this Form 8-K and the information contained in Exhibit 99.1 to this Form 8-K shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, and shall not be incorporated by reference into any filing under the Exchange Act or the Securities Act of 1933, as amended, except as shall be expressly set forth by specific reference in such filing.