Summary
You have from October 15 through December 7, 2026 to make Medicare changes, and whatever you choose takes effect January 1, 2027. Before you pick a drug plan, get an exact list of every medication you take, with the strength and how often, check that each one is on the plan's drug list, check that your pharmacy is in the plan's network, and compare your total yearly cost, not just the monthly premium. Your pharmacist can help with the list. Free, unbiased plan counseling in Illinois is available from SHIP at 1-800-252-8966.
Every fall, people come to our counter holding a stack of plan mailers and asking the same thing: "Which one should I pick?" We can't choose a plan for you, and we don't sell insurance. But a lot of what decides whether a plan works for you comes down to your medications, and that's where a pharmacist can help. Here are the questions worth asking, and what to do with the answers.
When is Medicare open enrollment, and what can I change?
Open enrollment opens October 15 and closes December 7, 2026. During those weeks you can join, switch or drop a Medicare Advantage plan, switch between Original Medicare and Medicare Advantage, and join, switch or drop a stand-alone Medicare drug plan (Part D) if you have Original Medicare. Your new coverage starts January 1, 2027, as long as the plan gets your request by December 7.
If you're already in a Medicare Advantage plan, there's a second window from January 1 to March 31 when you can switch to a different Medicare Advantage plan or go back to Original Medicare. It's a safety net, not a reason to wait.
What changes for Part D drug coverage in 2027?
The number that matters most is the yearly ceiling on your own spending for covered Part D drugs. Medicare.gov lists these 2027 amounts:
- The out-of-pocket cap goes up to $2,400 in 2027 (it was $2,100 in 2026). Reach it, and covered drugs cost you nothing for the rest of the year.
- The highest deductible any plan can charge goes up to $700, from $615. Some plans have no deductible at all.
Those are the most a standard plan can charge. Many plans charge less, which is exactly why comparing with your real drug list matters. Two people with the same plan can have very different yearly costs depending on what they take.
Questions to ask your pharmacist before you choose a plan
1. Is my medication list complete and exact?
This is the single most useful thing to bring to any plan comparison. You want every prescription with its exact name, strength and how often you take it. "My blood pressure pill" isn't enough: a plan might cover one strength or form and not another. Ask your pharmacist to look it over with you. If you use more than one pharmacy, bring all your bottles so nothing gets missed.
2. Is there a generic or lower-cost option for anything I take?
Sometimes there's a generic, a different strength, or a similar medication that plans cover more cheaply. Your pharmacist can point out where an option might exist. Any switch is your doctor's decision, so if something looks promising, ask your doctor at your next visit or let us reach out to their office.
3. Which of my medications usually need extra approval?
Some plans require a prior authorization (the plan has to approve a drug before it pays), step therapy (you try a lower-cost drug first), or quantity limits. These rules vary by plan. Ask us which of your medications have run into these rules before, then check how each plan you're considering handles them.
4. Will I be able to keep using this pharmacy?
Pharmacy networks change from year to year. Some plans also have "preferred" pharmacies where your copay is lower. When you compare plans on Medicare's website, add Orland Pharmacy as your pharmacy so each plan's estimate reflects what you'd pay here. You can also call us at (708) 726-5700 and ask about any plan you're considering.
5. Do I need to switch at all?
Maybe not. If your current plan still covers your medications at a cost you're comfortable with and still includes your pharmacy, staying put can be a fine choice. Your plan mails an Annual Notice of Change each fall. Read it, or bring it in, and look for changes to your drugs, your costs and the pharmacy network.
6. Can I spread my drug costs out over the year?
Yes, through the Medicare Prescription Payment Plan. It's free to join, and instead of paying each fill in full, your plan bills you in pieces across the calendar year. The total stays the same, so it mostly helps people who expect large drug costs in the first months of the year. Medicare says it usually isn't worth starting late in the year. Your plan handles sign-up.
7. Who can help me compare plans without selling me one?
In Illinois, the Senior Health Insurance Program (SHIP), run by the Illinois Department on Aging, offers free one-on-one Medicare counseling. SHIP counselors don't sell insurance and aren't tied to any insurance company. Call 1-800-252-8966. You can also call 1-800-MEDICARE (1-800-633-4227) or use the plan comparison tool at Medicare.gov.
How do I compare plans using my own drug list?
- Get your complete medication list (question 1 above).
- Go to Medicare.gov/plan-compare, or ask a family member or SHIP counselor to do it with you.
- Enter every medication, with strength and how often you take it.
- Add your pharmacy. If that's us, search for Orland Pharmacy in Homer Glen.
- Sort by total estimated yearly cost (drug costs plus premiums), not just the monthly premium.
- Check the details for each drug: covered or not, and any prior authorization, step therapy or quantity limits.
What mistakes do people make during open enrollment?
- Choosing on premium alone. A $0 premium plan can cost more over a year if your medications land on a high-cost tier.
- Leaving a medication off the list. Inhalers, eye drops, insulin and once-a-month medications are the ones people most often forget.
- Not checking the pharmacy. Your favorite pharmacy may be out of network or non-preferred on a new plan.
- Waiting until the last week. Help lines and counselors get busy in December. Start early.
Where can I get help with my medication list near Homer Glen and Orland Park?
Stop by Orland Pharmacy at 14322 S Will Cook Rd in Homer Glen, just south of 143rd Street next door to Advanced Physicians, or call (708) 726-5700. Bring your medications or your plan's Annual Notice of Change and ask us your questions. If you're thinking about moving your prescriptions to us for the new year, a transfer is free and we make the call to your old pharmacy. And if getting to a pharmacy is the hard part, we deliver prescriptions free anywhere in Illinois.
A quick note. This guide is general information. Orland Pharmacy does not sell insurance or recommend specific Medicare plans. Plan costs, drug lists and networks vary, so confirm details with the plan, Medicare or a SHIP counselor before you enroll.
Dates and enrollment rules checked October 2026 against Medicare.gov: joining a plan (opens in a new tab). 2027 Part D figures from Medicare.gov: Part D costs (opens in a new tab). Payment plan details from Medicare.gov: Medicare Prescription Payment Plan (opens in a new tab). SHIP details from the Illinois Department on Aging (opens in a new tab).
