Resources
Medicare FAQs for Chicago Seniors
These are the Medicare questions Chicago seniors bring up at kitchen tables, church halls and over the phone across the city. Don't see yours below? Call 773-250-9965. We'd rather talk it through than let you guess.
- Direct answers, no sales script
- Built around Chicago and Cook County
- Updated as the rules shift

Questions
What Chicago Medicare shoppers ask us most
Does it cost anything to work with Chicago Senior Insurance?
Nothing. Insurance carriers build the same commission into the plan price whether you enroll through an agent or on your own, so our help doesn't add a dime to your premium.
When can I first enroll in Medicare?
Most people get a seven-month Initial Enrollment Period: three months before your 65th birthday month, the birthday month, and three months after. Sign up early so your coverage isn't delayed.
Can I keep my current doctors?
With Original Medicare and a Medigap plan, yes, any provider who takes Medicare works. With a Medicare Advantage plan it comes down to the network. We check your Northwestern Memorial, Rush or UChicago Medicine doctors against each plan's current directory before you sign anything.
Is Medicare Advantage better than Medigap?
Neither wins for everyone. Medigap runs higher monthly but leaves you with almost nothing to pay when you actually get care, and no network to worry about. Advantage costs less each month but uses copays, a network, and usually folds in drug coverage and extras. The right pick depends on your doctors, your prescriptions, and how much cost swing you can handle.
What happens if I don't sign up for Part B on time?
Unless you're still covered through active employment, Medicare tacks on 10% to your Part B premium for every full 12 months you waited, and that surcharge sticks around for as long as you have Part B. Run the numbers on our Part B penalty calculator.
I don't take any prescriptions. Do I still need Part D?
Usually, yes. Go 63 days or more without creditable drug coverage once you're eligible and you trigger a penalty that never goes away. A cheap plan today beats that penalty almost every time.
Do I have to change plans every year?
No, but check anyway. Networks, drug tiers and copays reset every January 1. A quick review each fall, fifteen minutes at most, tells you whether your plan still fits.
Which hospitals do Chicago Medicare plans use?
Most Chicago seniors we work with land at Northwestern Memorial, Rush University Medical Center or UChicago Medicine, with neighborhood clinics filling in primary care. Which hospitals a plan covers changes year to year, so we confirm the current network before you commit to a plan year.
Can you help if I'm under 65 and on Medicare due to disability?
Yes. Illinois handles under-65 Medicare beneficiaries differently, especially for Medigap. We'll walk you through exactly what's open to you.
Do you serve towns outside Chicago?
We cover Cook County and the surrounding suburbs, from Lincoln Park and Hyde Park to Evanston, Oak Park, Skokie and Naperville.
Still on the basics? Start with the Medicare overview and the Medicare checklist.
Nothing to sign
Got a question we skipped?
Call and ask. It's free and there's no pressure to enroll. A lot of these calls end with you staying exactly where you are.
