Medicare Advantage

Medicare Deadlines in Chicago: What LIS Enrollees Should Watch

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.

CHICAGO — If you take Medicare drug coverage seriously, the calendar matters as much as the coverage itself. For Chicago residents who qualify for the Low-Income Subsidy (LIS, also called Extra Help), the choices for 2027 are wide — and a set of enrollment windows that don't all work the same way. Miss one, and your next chance may be months away.

Cook County has 58 Medicare Advantage plans available for 2027, offered by 11 carriers with drug coverage built in. That's still a lot to sort through, and LIS makes the sorting easier because it caps what you pay for covered drugs. But the help only reaches you if you're enrolled in a plan during a window when Medicare will accept your choice.

The two windows every Chicago enrollee should know

The Annual Enrollment Period (AEP) runs from October 15 to December 7 each year. This is the main window to join, switch, or drop a Medicare Advantage plan or a Part D drug plan. Anything you choose during AEP starts on January 1.

The Medicare Advantage Open Enrollment Period (MA-OEP) runs from January 1 to March 31. It's narrower: it's only for people already enrolled in a Medicare Advantage plan, and you can make one change — switch to a different MA plan, or drop MA and go back to Original Medicare (with a stand-alone Part D plan, where available).

Note that Illinois has 10 stand-alone Part D plans for 2027, sold statewide, so Cook County retirees on Original Medicare can pair their coverage with a PDP or instead get drug coverage bundled into a Medicare Advantage plan. That makes the AEP choice especially important — it's the main moment to line up your drug coverage for the year.

What LIS adds to the calendar

If you qualify for Extra Help, Medicare gives you an extra tool most people don't have: a Special Enrollment Period for LIS. People with LIS can change their Part D or MA-PD plan once during each of the first three calendar quarters (January–March, April–June, July–September). In the fourth quarter, everyone uses AEP.

That means an LIS-eligible Chicagoan isn't locked in the way a full-price enrollee is. If a plan stops covering a drug you need, or your pharmacy stops being in-network, you have a built-in chance to move.

What happens if you miss a window

Missing AEP is the most common misstep. If December 7 passes and you didn't act:

• If you're already in a Medicare Advantage plan, you can still use the January 1–March 31 MA-OEP to make one change.
• If you're on Original Medicare without drug coverage, you generally have to wait until the next AEP — unless a Special Enrollment Period applies (moving, losing other coverage, gaining or losing LIS, and a few other life events).
• Going without creditable drug coverage for 63 days or more can trigger a Part D late enrollment penalty that stays with you. People with LIS are protected from this penalty while they qualify — one more reason to confirm your LIS status each year.

How the dates interact with 2027 costs

A few Part D figures are set for 2027, and knowing them helps you compare plans during AEP:

• $2,400 is the most you'll pay out of pocket for covered Part D drugs in 2027 (up from $2,100 in 2026).
• $700 is the highest deductible a Part D plan can charge in 2027 (up from $615 in 2026).
• The old "donut hole" coverage gap was eliminated in 2025, so Part D now has three phases instead of four.
• The Medicare Prescription Payment Plan lets you spread your drug costs into monthly bills instead of paying at the pharmacy counter. You can opt in at any time during the year.
• IRMAA surcharges on Part B and Part D premiums start above $109,000 in income for a single filer in 2026. LIS and IRMAA are separate programs — qualifying for one doesn't affect the other.

A simple timing plan for Chicago residents

1. Before October 15: Check whether you still qualify for LIS. The Social Security Administration and Illinois Medicaid handle applications. 2. October 15 – December 7: Compare your options on Medicare.gov's Plan Finder. Enter your drugs and pharmacy to see how each plan handles them. 3. January 1: Your new coverage begins. 4. January – September: If you have LIS and something changes, remember you have one plan change per quarter. 5. All year: If drug costs are a strain, ask about the Medicare Prescription Payment Plan.