Getting started
Turning 65 in Chicago, IL
Turning 65 starts a Medicare clock, whether you're near the Loop or out in Norwood Park. You get a seven-month Initial Enrollment Period: three months before your birthday month, the birthday month itself, and three months after.
Sign up in the three months before your birthday and coverage starts the first of your birthday month. Wait, and your start date slides back. That's why we tell clients across Cook County to have this conversation at 64 and a half, not 65.
- A 7-month Initial Enrollment Period
- Different rules if you're still working
- Your one guaranteed Medigap window
- Free, local guidance from someone in Chicago
Your dates
Turning 65 enrollment calculator
Find your Medicare enrollment window
Enter your date of birth and get your Initial Enrollment Period, the month to apply, when coverage can start, and what matters if you're still working. Then a licensed agent can walk through it with you.
Timeline
What to do, and when to do it
- 1
3-6 months before your birthday
Decide if you're taking Part B now or holding off because of active employer coverage. Start pulling together your doctor and prescription lists.
- 2
3 months before
Sign up for Part A and Part B through Social Security if benefits haven't started automatically. If they have, your card shows up on its own.
- 3
2 months before
Pick your path: Original Medicare with a Medigap plan and Part D, or a Medicare Advantage plan. Check whether your Rush University Medical Center or Northwestern Memorial doctors are in-network.
- 4
1 month before
Get the application in so your ID cards arrive before your effective date. Make sure nothing lapses from your current coverage.
- 5
After your birthday
Your six-month Medigap open enrollment window starts when Part B begins. Use it. It's the only stretch where your health history doesn't matter.
Still working?
An employer plan changes the math
If you or your spouse are still working and the employer plan covers 20 or more people, you can typically delay Part B with no penalty and stay on the work plan. Most people still enroll in Part A since it's usually free, unless you're contributing to an HSA, since any part of Medicare stops that.
Once the job ends, an eight-month Special Enrollment Period opens for Part B. COBRA and retiree coverage don't stretch that window further. Getting this wrong is the costliest mistake we see, and you can run the numbers with our Part B penalty calculator.
Small employers work differently
Under 20 employees, Medicare usually becomes primary at 65, and delaying Part B can leave real gaps in your coverage. Check with HR before you decide anything.
Choosing
Two paths from here
- Original Medicare + Medigap + Part D: any doctor who takes Medicare, higher monthly cost, very few surprises
- Medicare Advantage: lower premium, a defined network, copays as you go, extras like dental and vision
- Both still require your monthly Part B premium
- Compare both, free, with an independent agent who works Chicago and Cook County
Read more about Medigap and Medicare Advantage, or work through the Medicare checklist first.
Get your enrollment timeline reviewed
We confirm your dates, tell you if your employer coverage lets you delay Part B, and lay out both coverage paths side by side. No cost, no pressure to sign anything.
Chicago Senior Insurance
A licensed local team, not a call center
Independent Medicare agency licensed in Illinois, based in Chicago, IL. Weekdays 8:30am to 5:30pm Central.
How we work, licensing and carriers →- Independent agency licensed in Illinois
- AHIP Medicare certified every plan year
- We check Northwestern, Rush, UChicago and Advocate networks first
- Zero cost for the review, now or later
- Office, phone and at-home appointments across Cook County
Written and checked by the licensed Medicare team at Chicago Senior Insurance, an independent medicare agency licensed in illinois. Last checked: July 2026.
Nothing to sign
Turning 65 this year?
We'll map your dates, check your doctors, and lay out both paths, free and with no obligation to enroll.