Medicare Made Simple: Free Library Sessions to Help You Prepare for 2027 Enrollment

September–November 2026

Medicare can feel complicated, but you don’t have to navigate it alone. This fall, Chicago Public Library is offering a series of free, in‑person programs designed to help older adults, caregivers, and anyone approaching age 65 understand their Medicare options. The Annual Enrollment Period is from October 15 to December 7, 2026. 

Whether you are enrolling for the first time, reviewing your current coverage, or helping a loved one choose a plan, these sessions will provide clear, practical guidance to support confident decisions. 

What You’ll Learn 

Across our Medicare programs, you’ll gain information about:
• The differences between Medicare Parts A, B, C & D
• Medicare Advantage vs. Medicare Supplement plans
• Prescription drug coverage (Part D)
• Eligibility and enrollment periods
• Costs, considerations, and coverage updates
• Planning ahead for 2027 Medicare decisions 

Programs are led by trusted partners, including Medicare Teacher, SMART Wealth Strategies, and licensed SHIP/ASI counselors. 

 

Upcoming Medicare Programs 

Medicare Made Simple
Led by SMART Wealth Strategies 
Medicare 101 
Presented by Medicare Teachers 
Learn About Medicare Options
Led by SHIP Counselors from ASI 
Who Should Attend? 
  • Adults approaching age 65
  • Anyone interested in reviewing or changing their Medicare plan
  • Caregivers supporting older adults
  • Community members wanting to better understand how Medicare works 

All sessions are free and open to the public.
No registration is required unless noted in the event listing. 

Stay Informed 

Visit our Events Calendar to explore all upcoming Medicare programs and find a session near you. CPL is here to help you make confident healthcare decisions for 2026–2027.