SentinelFamily Insurance
Medicare·6 min read

Turning 65 in Illinois: Your Medicare Enrollment Checklist

A month-by-month checklist for Illinois residents turning 65. What to do, what to avoid, and when to call a broker.

Key Takeaways

  • 1
    Start 6 months before your 65th birthday, not the month of.
  • 2
    Enroll in Medicare Part A and B through Social Security (online at ssa.gov, by phone, or in person).
  • 3
    Decide between Medigap + Part D OR Medicare Advantage during your Initial Enrollment Period.
  • 4
    Missing your Initial Enrollment Period can mean lifetime late-enrollment penalties.

6 months before your birthday

Schedule a free Medicare planning call. Decide whether you'll keep working past 65 (and stay on employer coverage) or transition fully onto Medicare.

If you'll be on Medicare, list your current physicians, your medications and dosages, and confirm your preferred hospital system in the Northwest Suburbs.

3 months before your birthday

Enroll in Part A and Part B at ssa.gov/medicare. Coverage starts the first day of your birthday month.

Compare Medigap quotes from carriers we represent. This is your best window — no underwriting required.

Birthday month

Your Medicare card arrives. Choose your Part D drug plan (if going with Medigap) or your Medicare Advantage plan (if going with Advantage).

Verify your physicians are in network for whatever you select.

After your birthday

You have 3 more months in your Initial Enrollment Period to make a final choice. After that, you can only switch during AEP (Oct 15 – Dec 7) or a Special Enrollment Period.

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