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Chicago · Cook CountyIndependent Medicare agency serving all 77 Chicago neighborhoods.

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Medicare Checklist for Chicago Seniors

Good Medicare decisions start with good information. Almost every problem we untangle traces back to something small: a drug left off a list, a specialist nobody checked, a letter from HR that never got requested.

Work through this list before you compare plans. It takes about twenty minutes, the same twenty minutes we spend with clients across Chicago.

  • What to pull together before comparing plans
  • Deadlines you can't afford to miss
  • Questions worth asking any agent
Quiet residential street in the Chicago, Illinois area

Step 1

Gather your documents

  • Your red, white and blue Medicare card, or your Social Security confirmation letter
  • Your current insurance card and plan name, if you have coverage today
  • Your Annual Notice of Change letter, if a plan mailed you one this fall
  • A creditable coverage letter from an employer, TRICARE or the VA
  • A rough sense of household income, in case Extra Help applies to you

Step 2

List what you actually use

  • Doctors and hospital

    Primary care, every specialist, and which system you lean toward, Northwestern Memorial, Rush University Medical Center or UChicago Medicine.
  • Prescriptions

    Exact drug names, dosages, how often you take them, and your pharmacy. Snap a photo of the bottles if that's quicker.
  • Expected care

    A planned surgery, ongoing therapy or regular lab work should steer which plan makes sense.

Step 3

Know your dates

  • Your 65th birthday and the seven-month Initial Enrollment Period around it
  • The day Part B starts, which kicks off your six-month Medigap window
  • October 15 through December 7 for Annual Open Enrollment
  • January 1 through March 31 if you're already on a Medicare Advantage plan
  • Your last day of active employment, if you're delaying Part B

Not sure which window applies to you?

Read Turning 65 if you're just getting started, or Switch Your Plan if you're already enrolled.

Step 4

Questions to ask any agent

A real independent agent should answer each of these without hedging: Which companies are you appointed with? Are my doctors in-network on this exact plan for next year? What will each of my prescriptions cost under this plan's formulary? What's my total expected cost for the year, not just the monthly premium? What happens if I need to switch later?

Vague answers mean keep shopping. Read about how we work or start with the FAQs.

Nothing to sign

Checklist done? Let's compare plans.

Bring what you've gathered and we'll line up the Cook County plans we represent side by side against your doctors and prescriptions.