Medicare Advantage in Chicago, Illinois: 2027 Coverage, Explained

Cook County's Medicare Advantage lineup shifts for 2027: 6 new plans, 17 plans leaving and 21 plans changing, out of the 78 offered for 2026. Here's a plain-English look at how the plans work for people in Chicago, Illinois and what to weigh — with no sales pitch.

67 Medicare Advantage plans are available for 2027. Because Chicago is served by Cook County (part of Chicagoland), those are the options on the table locally. Roughly 45% of people with Medicare in the county have chosen Medicare Advantage over Original Medicare, among the roughly 827,156 residents who are 65 or older.

It surprises people, but Medicare plan availability is drawn up county by county rather than by city or state — which is why a guide like this attributes everything to the surrounding county.

Read on for the organizations offering coverage in the area, a plain-language tour of how Medicare works, 2027 costs, enrollment timing, and free places to get unbiased help. We don't rank or recommend specific plans.

How your Medicare choices fit together

Almost everyone starts with Original Medicare — Part A (hospital) and Part B (medical), run by the federal government. From there, you generally choose one of two directions, and understanding the fork is the whole game.

The Medicare Advantage path (Part C). You get your Part A and Part B benefits through a private plan approved by Medicare, usually with drug coverage included. Plans work within networks and service areas set at the county level, which is why availability in Chicago, Illinois depends on your county, not just your state.

The Original Medicare path. You stay with the government program and can add a stand-alone Part D drug plan, and often a Medigap policy to help with the out-of-pocket costs Original Medicare leaves behind — trading bundled extras for broad provider freedom.

Neither path is universally better; the right fit depends on your doctors, your prescriptions, your budget, and how you like to handle care. This guide explains how each works in Chicago, Illinois so you can decide for yourself. We don't rank or recommend specific plans.

The 2027 numbers, from shared to plan-specific

Start with what's fixed for everyone. The standard Part B premium is $202.90 per month in 2026 (2026 amount; 2027 figure will be posted when CMS releases it), and Part A is premium-free for most people who paid Medicare taxes long enough while working.

On the drug side, Part D has real guardrails for 2027: a deductible capped at $700 and, a hard $2,400 ceiling on your out-of-pocket costs for covered prescriptions — the old coverage gap is gone.

Higher earners pay more for Parts B and D through an income-related adjustment called IRMAA, which for 2026 starts above $109,000 in annual income for an individual and is based on your 2024 tax return. Most people fall below that line and pay the standard amounts. The 2027 brackets will be posted when CMS releases them.

Everything past that is plan-specific: the premiums, copays, and coverage details of an individual Advantage or Medigap plan change from plan to plan and year to year. Rather than quote or rank those, we point you to Medicare's Plan Finder and a licensed agent for your exact numbers.

When you can enroll or make changes

Medicare's enrollment windows are federal — the same nationwide — so the timing below applies wherever you live.

Your first window (IEP). When you're new to Medicare, your Initial Enrollment Period is the 7-month window around your 65th birthday month. Signing up on time helps you avoid late penalties that can follow you for years.

Annual Enrollment Period (AEP). Each fall, from October 15 – December 7, anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan. Changes take effect January 1.

Medicare Advantage Open Enrollment. From January 1 – March 31, if you're already in an Advantage plan you get one chance to switch plans or return to Original Medicare.

Special Enrollment Periods can also open after certain life events, like moving or losing other coverage. The interactive calendar further down lays the year out visually.

Where to get free, unbiased help near Chicago

Good Medicare help exists and it's free — you don't have to figure this out solo or pay for guidance.

For official specifics and the Plan Finder tool, go straight to Medicare.gov or 1-800-MEDICARE (TTY 1-877-486-2048). And a licensed agent can compare options and handle the paperwork with you.

One note on who we are: MyMedicarePlans.org is an independent, privately owned educational resource — not Medicare, not a government agency, and not affiliated with one. Our job is to help you get oriented, then hand you off to the official sources and licensed professionals for plan decisions.

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