Every fall, Illinois seniors get a stack of mail from their Medicare plans. Most of it gets set aside. That’s understandable, but it can be costly. Medicare Open Enrollment runs from October 15 through December 7, and it’s the main time each year you can freely change your coverage for the year ahead. Plans change their premiums, drug lists, and doctor networks every year. The plan that worked well for you in 2026 may not be the best fit for 2027.
This article covers what to look at during open enrollment, the questions worth asking before you renew or switch, and one gap no plan change will fix. It also covers where a firm like Voorn, Preston, & Carlasare, PLLC can help you get the rest of your planning in order while you’re already thinking about the future.
Key Takeaways
Here’s a quick rundown of what you need to know about Medicare open enrollment.
Medicare Open Enrollment runs October 15 through December 7, and changes take effect January 1.
Your plan’s Annual Notice of Change is the most important document to read this fall, because it lists exactly what’s different next year.
Premiums are only part of the cost. Deductibles, copays, drug tiers, and out-of-pocket maximums often matter more.
No Medicare plan, Original or Advantage, covers long-term custodial care, so open enrollment is a good time to think about that gap separately.
Open enrollment is also a natural checkpoint for your healthcare power of attorney and other planning documents.
What Can You Change During Open Enrollment?
During the open enrollment window, you can switch from Original Medicare to a Medicare Advantage plan or back again. You can move from one Advantage plan to another, and you can join, drop, or switch a Part D prescription drug plan. If you do nothing, your current plan usually renews automatically, even if its costs or coverage have changed.
Medigap works differently. Open enrollment does not give you a guaranteed right to buy or switch a Medigap supplement policy. In most cases, insurers can review your health history before approving a new policy. If you’re thinking about moving from a Medicare Advantage plan back to Original Medicare with a Medigap policy, check whether you’d qualify for the supplement before you make the switch.
Illinois does offer some flexibility for people who already have a Medigap policy. If you’re between 65 and 75, you get a 45-day window each year starting on your birthday to switch to a plan with equal or lesser benefits from your current insurer or its affiliate, with no health questions. This rule doesn’t apply if you’re coming from a Medicare Advantage plan and don’t already have Medigap.
What Should You Review This Year?
Start with your Annual Notice of Change. Your plan must send this by September 30. It spells out every change for the coming year: premiums, deductibles, copays, covered drugs, and network changes. If you read only one document this fall, make it this one.
Check your prescriptions against next year’s formulary. Drug plans regularly move medications to different cost tiers, add prior authorization requirements, or drop drugs entirely. Make a current list of every medication you take, with dosages, and confirm each one is still covered in 2027 and what it will cost. Medicare’s Plan Finder tool at Medicare.gov lets you enter your exact drugs and compare plans side by side.
Look at total cost, not just the premium. A plan with a $0 premium can still cost you more over the year than one with a monthly premium, depending on its deductible, copays, and how your medications are tiered. For Medicare Advantage plans, look at the maximum out-of-pocket limit. That’s the most you’d pay for covered medical services in a bad year. Part D now has an annual cap on out-of-pocket drug costs, and the Medicare Prescription Payment Plan lets you spread those costs over monthly payments instead of paying large amounts at the pharmacy counter.
Confirm your doctors and pharmacy are still in network. This is especially important with Medicare Advantage plans, where networks can change from year to year. Call your primary care doctor, your specialists, and any hospital you’d want to use, and ask whether they’ll accept your plan next year. Check whether your pharmacy is “preferred” in your drug plan’s network, since that can change your copays significantly.
Consider how your health has changed. A new diagnosis, an upcoming surgery, or more frequent specialist visits can make a different plan a better fit. If you expect to need more care next year, a plan with higher premiums but lower out-of-pocket costs may save you money.
Think about travel and time away. If you spend winters in another state or visit family out of state for long stretches, check how your plan handles care outside its service area. Many Advantage plans offer limited coverage away from home.
Look closely at “extra” benefits. Dental, vision, hearing, fitness memberships, and grocery or transportation allowances are common selling points for Advantage plans. They can be valuable, but they’re often capped at modest amounts and can change from year to year. Don’t let them outweigh the core question of whether the plan covers your doctors and drugs affordably.
See whether you qualify for help with costs. Illinois residents with limited income may qualify for Extra Help with drug costs or a Medicare Savings Program that helps pay premiums and cost-sharing. Many people who qualify never apply.
If this feels like a lot, Illinois offers free, unbiased counseling through the Senior Health Insurance Program (SHIP), run by the Illinois Department on Aging. SHIP counselors can walk you through plan comparisons without selling you anything.
The Gap Open Enrollment Won’t Fix
Whatever plan you choose, one thing stays the same: Medicare does not cover long-term custodial care. Custodial care covers help with daily activities like eating, bathing, dressing, and moving around, and research on long-term services and supports for older Americans shows it makes up the bulk of what long-term care actually looks like for most families. Recent estimates suggest a majority of people turning 65 will need some form of long-term care during their remaining years, and a nationwide planning and progress study found most Americans expect to face a long-term care event themselves, which makes this far more than a rare exception.
Medicare does step in for a limited stretch of skilled nursing care, as outlined in official Medicare long-term care coverage details, but only when specific conditions line up in the right order. You must first spend at least three days as an admitted hospital patient (not under observation status), then move into a Medicare-certified skilled nursing facility within 30 days of discharge, and the care you receive there must require a nurse or therapist rather than basic personal assistance. Miss any one of those conditions, and Original Medicare won’t cover the stay. Some Medicare Advantage plans waive the three-day hospital requirement, but they may require prior approval instead.
When the conditions are met, Medicare’s coverage still runs out fast, which is exactly why so many Illinois families get caught off guard. Under Original Medicare, the payment schedule breaks down like this:
Days 1 through 20 are covered in full by Medicare Part A, so you owe nothing out of pocket during this window as long as you keep meeting the skilled care requirement.
Days 21 through 100 require a daily copayment that adjusts each year, with Medicare covering the remaining cost of your care during that stretch.
After day 100 in that benefit period, Medicare stops paying entirely, and you become responsible for the full cost of continued nursing home care.
Some Medicare Advantage plans advertise in-home support benefits, but these are small supplements, not long-term care coverage. Families usually end up paying for custodial care through savings, long-term care insurance, VA benefits for eligible veterans, or eventually Medicaid once they meet Illinois’s strict income and asset limits. Open enrollment won’t close this gap, but it’s a good reminder to think about it before you need care rather than during a crisis.
Use Open Enrollment as a Planning Checkpoint
Since you’re already reviewing your healthcare coverage, it’s a natural time to make sure your legal documents are ready too. A few questions are worth asking each fall:
Do you have a healthcare power of attorney naming someone to make medical decisions if you can’t?
Does that person know your wishes, and can they find the document quickly?
Have you signed a HIPAA authorization so family members can speak with your doctors and your Medicare plan on your behalf?
Is your property power of attorney current, and does your estate plan reflect how you’d want to pay for care if you needed it?
Voorn, Preston, & Carlasare, PLLC helps Illinois families put these documents in place and update them as circumstances change. That includes estate planning, elder law counsel, and guidance on preparing for future care costs, so that a health event doesn’t also become a legal scramble for your family.
The Takeaway
Medicare Open Enrollment is your yearly chance to make sure your coverage still fits your health, your medications, and your budget. Read your Annual Notice of Change, compare your total costs, confirm your doctors and pharmacy, and don’t let a plan renew automatically without a second look. Keep in mind that no plan choice will cover long-term custodial care. That’s a separate planning question, and it’s worth addressing well before it becomes urgent. If you’d like to talk through your healthcare directives or long-term care planning, contact Voorn, Preston, & Carlasare, PLLC to schedule a conversation.
Frequently Asked Questions
What happens if I miss the December 7 deadline?
Your current plan will generally renew for the next year. If you’re in a Medicare Advantage plan, you’ll have another chance to switch plans or return to Original Medicare during the Medicare Advantage Open Enrollment Period, January 1 through March 31. Certain life events, such as moving or losing other coverage, may also qualify you for a Special Enrollment Period.
Should I switch plans if my current one is working fine?
Not necessarily, but you should still check. Plans change every year, so “working fine” in 2026 doesn’t guarantee the same costs or coverage in 2027. A quick comparison using your Annual Notice of Change and Medicare’s Plan Finder will tell you whether staying put still makes sense.
Does Medicare Advantage cover long-term care better than Original Medicare?
No. Advantage plans must cover everything Original Medicare covers, including the limited skilled nursing benefit, and some add small extras like home support allowances. None of them provide ongoing long-term custodial care coverage.
Where can I get free help comparing plans in Illinois?
The Senior Health Insurance Program (SHIP), through the Illinois Department on Aging, offers free one-on-one counseling. You can also call 1-800-MEDICARE or use the Plan Finder tool at Medicare.gov.
