Medicare open enrollment is here—and Chicagoans don’t have to sort through their options alone.
Through December 7, people with Medicare can review and change their Medicare Advantage or Part D prescription drug coverage for 2027. Changes made during this window take effect January 1, 2027.
Need a hand with the fine print? Illinois’ Senior Health Insurance Program (SHIP) offers free, one-on-one counseling for people with Medicare and their caregivers. Call 1-800-252-8966 to get connected.
From neighborhood senior centers to local library branches, here’s where to find help—and what to check before the deadline.
Your Medicare checklist for 2027
- Read your Annual Notice of Change. Your plan’s September notice outlines what will change next year. Pay particular attention to premiums, copays, and prescription drug costs.
- Don’t assume you have to switch. If your plan is still offered and you remain eligible, you’ll generally be automatically re-enrolled. Still, take a look at what’s changing before deciding to stay.
- Watch for a non-renewal notice. If your Medicare Advantage plan isn’t renewing for 2027, you have a Special Enrollment Period from December 8, 2026, through February 28, 2027. You can choose another Medicare Advantage plan or return to Original Medicare and join a separate Part D drug plan. If you don’t join another Medicare Advantage plan before your current coverage ends, you’ll be enrolled in Original Medicare.
- Know your second chance. If you’re already in Medicare Advantage, you can make one change between January 1 and March 31, 2027: switch to another Medicare Advantage plan or return to Original Medicare. If you return to Original Medicare, you can also join a separate drug plan. This isn’t a general enrollment window for people who only want to switch stand-alone Part D plans.
- Keep an eye on drug coverage. After your initial Part D enrollment period ends, going 63 consecutive days or more without Medicare drug coverage or other creditable prescription coverage can trigger a late-enrollment penalty. You’ll generally pay it for as long as you have Medicare drug coverage. People receiving Extra Help don’t pay this penalty.
Where to get free, in-person help in Chicago
Chicago’s SHIP counselors offer one-on-one appointments at the city’s Regional Senior Centers. They can help you understand Medicare, compare Part D options, navigate Medigap coverage, and resolve Medicare billing disputes.
Chicago Senior Centers
- Central West: 2102 W. Ogden Ave.
- Renaissance Court: 78 E. Washington St.
- Northwest/Copernicus: 3160 N. Milwaukee Ave.
- Northeast/Levy: 2019 W. Lawrence Ave.
- Southeast/Atlas: 1767 E. 79th St.
- Southwest: 6117 S. Kedzie Ave.
Your local library can help, too
Chicago Public Library is hosting free Medicare programs this fall for people approaching 65, caregivers, and anyone reviewing their coverage.
Sessions cover Medicare’s different parts, Medicare Advantage versus Medigap plans, prescription drug coverage, and enrollment periods. Registration isn’t required unless the event listing says otherwise.
Upcoming sessions led by SHIP counselors include:
- Little Village: Monday, October 26, 11 a.m.–12:30 p.m.
- Jeffery Manor: Tuesday, October 27, 1–2:30 p.m.
- Richard J. Daley: Friday, October 30, 11 a.m.–12:30 p.m.
- King: Thursday, November 5, 12:30–1:30 p.m.
- West Town: Friday, November 6, 10:30–11:30 a.m., in Spanish.
Prefer to start with a phone call? Contact Illinois’ Senior HelpLine at 1-800-252-8966 and ask to connect with a SHIP counselor.
