Medicare Plans
Medicare Mistakes to Avoid in Chicago
We've sat at kitchen tables from Beverly to Rogers Park, and the same handful of errors keep showing up. Rarely is it about picking the "wrong" plan. Usually it's a missed date, a bad assumption, or a decision made off a postcard.
Here's what to watch for before it costs you.
- Most mistakes stick for life, not just a year
- A single review catches almost all of them
- Missed deadlines hurt more than plan choice

The big ones
Seven Medicare mistakes that cost real money
1. Missing your Part B window
Without active employer coverage, a late Part B sign-up triggers a penalty that follows you for as long as you're on Medicare. Run the numbers on our Part B penalty calculator.2. Skipping drug coverage
Not filling any prescriptions right now doesn't protect you. Go 63 or more days without creditable drug coverage and you're stuck with a permanent premium add-on.3. Assuming last year's network still applies
Hospitals and physician groups renegotiate contracts every year. Check your doctors each fall instead of trusting last year's plan lineup.4. Choosing by premium alone
A $0 plan with the wrong drug tiers can cost you far more over twelve months than a plan with a modest monthly bill.5. Letting your Medigap window close
Your one guaranteed-issue window for Medigap opens when Part B starts and closes six months later. After that, Illinois carriers can ask health questions.6. Enrolling straight from a TV ad
National ads push one plan nationwide. They have no idea whether that plan works with Northwestern Memorial or Rush here in Chicago.
7. Never checking again
The costliest mistake is doing nothing. Plans reset every January 1, and a fifteen-minute check-in each Open Enrollment usually covers it.
Also worth knowing
Smaller missteps we fix constantly
Some people add a standalone Part D plan on top of a Medicare Advantage plan that already includes drugs, which can knock them out of the Advantage plan entirely. Others drop a Medigap policy expecting to grab it back later, only to fail underwriting. And plenty never mention a spouse's coverage, so we find out too late that a Special Enrollment Period was sitting there unused.
None of this is complicated. It's just detail work, and that's what a local independent agent handles for you. New to this? Read the Medicare overview and work through the Medicare checklist.
Nothing to sign
Worried you already made one of these?
Most are fixable if we catch them in time. Call 773-250-9965 for a free, no-judgment look at where you stand.
