Medicare Advantage

Medicare Part D in 2027: Chicago, IL Guide

For 2027, Chicago is looking at 67 Medicare Advantage plans: 6 new, 17 gone since 2026, and 30 still here but changed on premium, deductible, plan type or name, 9 of them under a new name. Below, how the lineup shifted in Cook County and what to compare, with no plan ranked or recommended.

How Part D works in 2027 for Chicago: the $2,400 out-of-pocket cap, $700 maximum deductible, and the payment plan.

CHICAGO — For Chicagoans on Medicare, 2027 brings a clearer picture of what prescription drugs can cost — and, for people with limited income, a program that can lower those costs even further. Understanding how the pieces of Part D fit together is the first step in deciding what makes sense for you this fall.

The 2027 cost pieces, in plain English

Part D — the prescription drug side of Medicare — is built out of a few standard cost pieces. Once you know what each one does, comparing options gets much easier.

• Premium. A monthly amount you pay for the plan itself. Premiums vary by plan and can change each year.
• Deductible. What you pay out of pocket before the plan starts sharing costs. For 2027, no Part D plan can set a deductible higher than $700. Some plans set it lower.
• Copay or coinsurance. Your share of each prescription after the deductible is met.
• Out-of-pocket cap. In 2027, once your out-of-pocket spending on covered drugs reaches $2,400, you pay nothing for covered drugs the rest of the year.

That cap ($2,100 in 2026, $2,400 in 2027) is a meaningful change from just a few years ago, when there was no annual ceiling at all on Part D drug spending.

The "donut hole" is gone

For years, Part D had a confusing middle phase called the coverage gap, or donut hole, where your share of drug costs jumped for a stretch. As of 2025, that phase was eliminated. Part D now moves through three phases: the deductible phase, the initial coverage phase, and the catastrophic phase (where you hit the cap and pay nothing more for covered drugs).

This is one of the biggest structural changes to Part D since the program began, and it carries into 2027 unchanged.

Smoothing the cost across the year

Hitting a deductible ($615 in 2026, $700 in 2027) in January can still sting, even if the annual cap is lower than it used to be. That's where the Medicare Prescription Payment Plan comes in. It's optional, and it lets you spread your out-of-pocket drug costs across the calendar year in monthly installments instead of paying at the pharmacy counter.

You don't save money using it — you pay the same total — but it can make a big pharmacy bill more manageable. You sign up through your drug plan.

A note on IRMAA at the top of the income scale

Most people pay the standard Part B and Part D premiums. But higher-income beneficiaries pay an extra amount called IRMAA (the Income-Related Monthly Adjustment Amount). For 2026, IRMAA surcharges kick in above $109,000 in income for a single filer (higher thresholds apply for joint filers). Social Security uses your tax return from two years earlier to decide.

If your income has dropped since then — say, because you retired — you can ask Social Security to reconsider.

How this looks in Chicago

Chicago is in Cook County, where Medicare beneficiaries have a wide field to compare. For 2027, Cook County has 58 Medicare Advantage plans available and 11 carriers offering Medicare Advantage plans that include drug coverage. With more than 827,000 residents age 65 and older, it's one of the largest Medicare markets in the country.

Plan availability is set at the county level, not the city level, so two neighbors in Chicago see the same menu of plans. What differs is which plan fits each person's doctors, medications and budget.

Deciding what to do this fall

The Annual Enrollment Period runs Oct. 15 through Dec. 7, 2026. That's your window to join, switch, or drop Part D or Medicare Advantage coverage for 2027. If you're already in a Medicare Advantage plan, you also get a second window — the Medicare Advantage Open Enrollment Period, Jan. 1 through March 31 — to make one change.

When comparing, focus on the cost structure as a whole, not just one number:

• What is the monthly premium?
• What is the deductible, and which drugs is it waived on?
• What will your specific medications cost through the year?
• Does the plan use the pharmacies you already use?

The official Plan Finder at medicare.gov lets you enter your drugs and pharmacies to see year-long cost estimates for each plan.

Where to get unbiased help

• medicare.gov — the official Plan Finder and enrollment tool.
• 1-800-MEDICARE (1-800-633-4227) — 24/7 help from Medicare directly.
• Illinois SHIP (Senior Health Insurance Program) — free, one-on-one counseling from trained volunteers who don't sell insurance. Reach it at 1-800-252-8966.
• Social Security — apply for Extra Help (the Low-Income Subsidy) at ssa.gov or 1-800-772-1213.