The 2027 Open Enrollment period for retiree health insurance will run from October 1-31, 2026. During this time, annuitants can enroll, add or drop a dependent, or change a health insurance plan. Changes become effective January 1, 2027.   

Open Enrollment Education
During Open Enrollment, CTPF offers webinars and in-person seminars to educate members about CTPF’s health insurance plans.         

Medicare Webinar

• Click here to register for the Open Enrollment Webinar - Medicare Plans on Thursday, October 1, 2026, at 10 a.m.
• Click here to register for the Open Enrollment Webinar - Medicare Plans on Friday, October 2, 2026, at 10 a.m.

Non-Medicare Webinar

• Click here to register for the Open Enrollment Webinar - Non-Medicare Plans on Thursday, October 1, 2026, at 1 p.m.

Open Enrollment In-Person Seminars   
CTPF will host in-person Open Enrollment Seminars on Tuesday, October 6, 2026, at the Hilton/Oak Lawn (9333 S. Cicero Ave., Oak Lawn, IL, 60453). The Medicare Seminar will be held at 9:30 a.m. and the Non-Medicare Seminar will be held at 1:30 p.m. Registration is required and opens on September 23, 2026. 

Open Enrollment Vendor Week
During Open Enrollment, CTPF vendors host information sessions for members who want to hear directly from health insurance plan vendors. Visit the CTPF Calendar for dates and registration information.

Visit Open Enrollment Central for more information.