Medicare Advantage (Part C)
One plan, one card, often with dental, vision, and drug coverage bundled in. We check whether your primary care doctor and specialists sit inside the networks we can offer.
Medicare Plans in Chicago, IL, Made Simple
Finding the right Medicare plan in Chicago shouldn't take a week of phone calls. We check your doctors, your prescriptions, and your real costs before pointing you toward Medicare Advantage, Medigap, or Part D.
Why Chicagoans call us
Licensed Illinois agents, no call center
- 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
We're an independent, Illinois-licensed agency. We don't carry every plan sold in Cook County, but we compare what we do offer and tell you straight which ones match your doctors, your medications, and your budget.
Written and checked by the licensed Medicare team at Chicago Senior Insurance, an independent medicare agency licensed in illinois. Last checked: July 2026.
What clients around Chicago are saying
Shown with permission, using each client's first name, last initial and neighborhood.
Turning 65
“I hit 65 in February and the paperwork order made no sense to me. One phone call sorted my dates. My Part B start was locked in and my plan was chosen weeks before my birthday.”
Doctor networks
“Keeping my cardiologist at Rush was the only thing I cared about. They pulled the network lists first and told me straight which plans kept that doctor and which ones did not.”
Prescription costs
“Instead of quoting a premium, they priced all six of my prescriptions against each drug list. My yearly cost fell and I still fill everything at the Walgreens two blocks away.”
Placeholder content: the quotes above are sample reviews used while building this site. Swap them for real client quotes and links to the public review profile, or drop this section, before the site goes live.
Three quick checks that actually matter
These are the questions that decide which plan fits, not whichever glossy mailer showed up first.
Find your Medicare enrollment window
Give us your date of birth and we'll map out your Initial Enrollment Period, when to apply, and when coverage could start.
Check my doctor's network
Give us the name of your doctor or clinic. Our licensed agents check it against the plans we offer in your ZIP code and calls you back with an answer, usually within one business day. No instant online guess, just a real check.
Check my prescription costs
The premium never tells the whole story. We run your medications against the drug lists of the plans we sell in your area, factor in your pharmacy, and call you with the real annual total, not just the monthly sticker price.
Annual Enrollment runs Oct 15 through Dec 7
Networks, drug tiers, and premiums shift every year in Chicago. A free review takes about 15 minutes and can save real money. See what to check this year
Turning 65 in the next six months?
Your Initial Enrollment Period opens three months before your birthday month. Miss it, and you could face a Part B penalty for life. Find my enrollment window
Medicare Coverage We Place Across Chicago, IL
We're independent, not tied to one insurance company. We lay out the options we can offer, walk through the trade-offs in plain language, and let your numbers make the call.
Medicare Supplement (Medigap)
Steady, predictable costs and the freedom to see any provider that takes Medicare, including specialists at Northwestern Memorial or Rush.
Part D Prescription Drug Plans
We take your exact medication list and run it against the formularies of the plans we represent, then show you the real yearly cost, not just the sticker premium.
Already on Medicare?
We'll give you a second opinion on the plan you already have. If it beats everything else we can offer, we'll say so and leave you alone.
Final Expense & Life
Straightforward whole-life coverage so funeral costs don't land on your family in Chicago. Some options need no medical exam at all.
Turning 65 soon
Your seven-month Initial Enrollment Period, your one guaranteed shot at Medigap, and what changes if you're still working past 65.
The real test: who answers your call three years from now?
Chicago Senior Insurance is a small, local Medicare agency. You won't get handed off to a script reader sitting in another state.
Call 773-250-9965- 01
You talk to the same person, year after year
No call center, no rotating reps. The agent who enrolls you is the one who answers when a claim looks wrong next January.
- 02
We check your doctors and your drugs before anything else
Before we recommend a single plan, we check your providers and run your prescriptions against what we offer. That step is where most Chicago seniors get burned skipping it.
- 03
None of this costs you anything
Carriers pay us, not you. Your premium doesn't change whether you work with us or go it alone.
- 04
We show up, in person, around Chicago
Home visits across Cook County, from Rogers Park to Beverly, plus phone or video if that fits your day better.
Why call us instead of 1-800-MEDICARE?
Both have their place. 1-800-MEDICARE and Medicare.gov can walk you through every plan sold in your area. We work with a shorter list of carriers, but we do the legwork on your doctors, prescriptions and budget ourselves.
| Working with Chicago Senior Insurance | 1-800-MEDICARE / Medicare.gov |
|---|---|
| A small Chicago team that keeps your file and remembers your case | A general help line staffed by whoever picks up |
| Checks your actual doctors and prescriptions before suggesting a plan | Gives general Medicare information and plan lookups |
| Same person handles you after enrollment, including at claim time | You may talk to someone new every time you call |
| Compares the carriers we represent in your ZIP code | Can tell you about every plan sold in your area |
| In-person, home and phone appointments anywhere in Cook County | Mostly phone-based, plus Medicare.gov self-service tools |
We don't sell every plan available where you live. To see the full list, contact Medicare.gov, 1-800-MEDICARE, or the Illinois State Health Insurance Assistance Program (SHIP).
How a Free Medicare Plan Review Works in Chicago
- 1
A quick 15-minute call
Call us or fill out the short form. We ask about your doctors, your medications, your budget, and what bugged you about your last plan.
- 2
A side-by-side comparison you can actually read
We price out the plans we can offer for your Chicago ZIP code, whether that's 60614 or 60629, and put it all on one page.
- 3
Enrollment, done together
We fill out the application with you, in person, by phone, or online. Most people are done in under 30 minutes.
- 4
A checkup every fall
Plans shift every October. We re-run your numbers each year and only suggest switching if the math backs it up.
Medicare Help Across Chicago and Cook County
Medicare networks are built block by block, not state by state. A plan that works great in Phoenix can leave you stranded in Chicago if your cardiologist at Northwestern Memorial or Rush isn't contracted. We check network lists from the plans we represent against your own doctors before we recommend anything.
We meet clients across Lincoln Park, Hyde Park, Pilsen, Wicker Park, Jefferson Park, and plenty of towns just outside city limits, and we work Medicare Annual Enrollment (Oct 15 through Dec 7) here in Cook County every single year.
Ready to Compare Medicare Plans in Chicago? No Pressure to Enroll
Most reviews wrap up in one short call. If your current plan already beats what we can offer, we'll tell you straight and let it be.
773-250-9965Mon to Fri, 8:30am to 5:30pm, Chicago, IL
- No fee, ever: the carriers we represent pay us, not you
- Licensed in Illinois and Medicare-certified every year
- The same advisor next year, and the year after that
Written and checked by the licensed Medicare team at Chicago Senior Insurance, an independent medicare agency licensed in illinois. Last checked: July 2026.
Medicare Questions We Hear Across Chicago, IL
- When can I enroll in Medicare in Chicago, IL?
- You get a seven-month window built around your 65th birthday month: three months before, your birthday month, and three months after. Every fall, Annual Enrollment opens October 15 and closes December 7. Move from Lincoln Park to Naperville, retire, or lose employer coverage, and a Special Enrollment Period kicks in too.
- Does it cost anything to work with your agency?
- Nothing. The carriers we represent pay us directly, and your premium is identical whether you sign up through us or go straight to the company yourself.
- Medicare Advantage or a Medicare Supplement, which fits me?
- It comes down to your doctors, how often you travel, your prescriptions, and your budget. We run the numbers on both, using the carriers we represent, before we tell you which one makes sense for your situation.
- Can you check whether my doctor is in network?
- Yes, every time. Before we suggest a single plan, we check your doctors against the networks we can offer, whether that's Northwestern Memorial, Rush University Medical Center, UChicago Medicine, or a smaller Cook County clinic, and we run your prescriptions against each plan's drug list too.
- Do you meet in person?
- We do. We visit clients at home across Lincoln Park, Hyde Park, Beverly, Jefferson Park, Albany Park and nearby suburbs. If a phone call works better for your schedule, that's fine too, plenty of Chicago clients handle the whole thing that way.