Using AI to Compare Medicare Plans During Open Enrollment

Everyday life Tutorial9 min read·Updated September 28, 2026

This article is for general information only and is not medical advice. For any health concerns, please consult a qualified healthcare professional.

The short answer

Medicare's annual Open Enrollment Period runs October 15 through December 7 every year, for coverage that starts the following January 1. AI tools like ChatGPT or Gemini can help you summarize and compare plan details you've already pulled from the official Medicare Plan Finder at medicare.gov/plan-compare — but they should never be the source of the numbers themselves, and you should never enter your Medicare number or personal details into a chatbot or website that contacted you first.

Every autumn, tens of millions of people with Medicare get a stack of mail: plan comparison booklets, an Annual Notice of Change letter, maybe a call from an insurance agent. Medicare's Open Enrollment Period runs October 15 through December 7 every year, and it's the one window where you can freely switch between Original Medicare and a Medicare Advantage plan, change plans, or join or drop a Part D drug plan — with the change taking effect January 1. It's also, understandably, the moment a lot of people wonder if ChatGPT could just do the comparing for them.

It partly can — but not the way you might expect. Here's how to use AI as a genuinely useful assistant in this process, without letting it (or a scammer pretending to be it) make the actual decision for you.

What AI Is Good For Here — and What It Isn't

AI is useful for:

  • Turning a dense Annual Notice of Change letter into a plain-English summary of what's actually different next year
  • Explaining unfamiliar terms — "formulary," "prior authorization," "Medigap," "star rating" — in context
  • Building a checklist of questions to ask an insurer, a doctor's office, or a SHIP counselor
  • Organizing a side-by-side comparison once you've already pulled the real numbers for two or three plans

AI is not reliable for:

  • Calculating your actual yearly cost for a plan — that depends on live premium, deductible, and drug-pricing data that only the official Medicare Plan Finder has
  • Confirming whether your specific doctors or pharmacy are in a plan's network this year
  • Telling you which plan is "best" without seeing your real prescriptions, providers, and location
  • Anything involving your Medicare number — that never belongs in a chat with a tool or a website that contacted you first

With that division in mind, here's a safe way to actually do this.

Start at the official Medicare Plan Finder, not a chatbot

Go to medicare.gov/plan-compare. You can browse plans without logging in, or sign in with your Medicare account to have your current drugs and pharmacies pre-filled. Enter every prescription you take and the pharmacy you use — this is the step that makes the cost estimates real, because the tool prices out your actual medications against each plan's formulary.

Narrow the list down to two or three plans that look reasonable. This is your source of truth for the rest of the process.

Read your Annual Notice of Change letter — with AI's help

If you're already on a Medicare Advantage or Part D plan, your insurer was required to send you an Annual Notice of Change (ANOC) letter by the end of September, listing what's changing for next year: premium, deductible, drug tiers, and network.

Copy the text of that letter (leaving out your Medicare number and other personal identifiers) into ChatGPT or Gemini and ask:

"This is my Medicare plan's Annual Notice of Change letter. Can you summarize in plain English what's changing next year, and flag anything that looks like it could cost me more?"

This is where AI earns its place in the process — a three-page notice written in insurance language becomes a short, readable list.

Ask AI to organize your comparison, using the Plan Finder's own numbers

Once you have real numbers from Step 1 for two or three plans — premium, deductible, and estimated drug costs — you can ask AI to lay them out side by side:

"Here are three Medicare plans with their premium, deductible, and estimated yearly drug cost from the Medicare Plan Finder: paste the numbers. Can you put these in a simple comparison table and note the biggest differences?"

Feeding it numbers you already trust, rather than asking it to produce numbers itself, is the difference between using AI as an organizer and using it as an unreliable source.

Watch for the Medicare-scam pattern

Enrollment season is also scam season. Consumer-protection groups have flagged a rise in AI-generated phone calls, fake "Medicare advisor" chatbots, and lookalike websites that appear during Open Enrollment specifically to harvest Medicare numbers and bank details.

A few rules that hold regardless of how convincing the caller or chatbot sounds:

  • Medicare and Social Security never call, text, or email you first to "confirm" your Medicare number or ask you to pay to keep your coverage active.
  • A real agent can wait. If someone is pressuring you to decide or hand over information immediately, that pressure is the warning sign, not the offer itself.
  • If you didn't start the contact, don't continue it. Hang up, close the page, and call 1-800-MEDICARE yourself to check whether anything is actually wrong with your account.

Get a free second opinion from a real person

Every state has a State Health Insurance Assistance Program (SHIP) — free, unbiased Medicare counseling with no ties to any insurance company. A SHIP counselor can review your plan options with you over the phone or in person, at no cost.

Find your local SHIP at shiphelp.org, or call 1-800-MEDICARE (1-800-633-4227), available 24 hours a day. If anything about your comparison still feels uncertain after using AI, this is the step that resolves it.

The One-Sentence Version

Let the official Medicare Plan Finder generate the real numbers, let AI turn those numbers and your Annual Notice of Change letter into something you can actually read and compare, and let a free SHIP counselor be your second opinion — and never let anyone who contacted you first be the one asking for your Medicare number.

If you also received a confusing government letter about Social Security or another benefit this season, our guide on using AI to understand government forms and benefits covers the same paste-and-ask approach in more detail.

Sources

Published September 28, 2026 · Updated September 28, 2026How we test →

Frequently asked questions

When exactly is Medicare Open Enrollment, and what does it change?
Medicare's annual Open Enrollment Period runs every year from October 15 through December 7. During this window, anyone with Medicare can switch between Original Medicare and a Medicare Advantage plan, change Medicare Advantage plans, join or switch a Part D prescription drug plan, or drop drug coverage entirely. Any change you make takes effect on January 1 of the following year. This is different from the Medicare Advantage Open Enrollment Period, which runs January 1 through March 31 and is only for people already enrolled in a Medicare Advantage plan who want one more chance to switch plans or move back to Original Medicare.
Can I trust ChatGPT or Gemini to tell me which Medicare plan is cheapest for me?
No — not as the final answer. General AI chatbots don't have live access to this year's plan premiums, deductibles, drug formularies, or your local provider network, and plan details change every year. The only tool that calculates your actual total cost — based on the real drugs and pharmacies you use — is the official Medicare Plan Finder at medicare.gov/plan-compare. Use AI to help you understand and organize what the Plan Finder shows you, not to generate the numbers from scratch.
Are there real scams involving AI and Medicare right now?
Yes. Consumer protection groups and Medicare counselors have reported a rise in scams that use AI-generated phone calls, fake chatbots, and professional-looking websites that mimic Medicare or an insurance company during enrollment season, then ask for your Medicare number or bank details. A safe rule: Medicare and the Social Security Administration will never call, text, or email you out of the blue asking to confirm your Medicare number. If you didn't start the contact, hang up or close the page and call 1-800-MEDICARE yourself to check.
What's the safest way to use AI in this process?
Do your research on official sites first — medicare.gov/plan-compare for plan details, your insurer's own published plan documents for a plan you're already considering. Then paste that text into ChatGPT or Gemini and ask it to summarize the differences in plain English, or to turn a dense Annual Notice of Change letter into a checklist. AI is a strong translator and organizer of information you already have; treat anything it tells you about specific costs or coverage as a draft to double-check, not a final answer.
Where can I get free, unbiased human help instead of using AI at all?
Every state has a State Health Insurance Assistance Program (SHIP) — free, impartial Medicare counseling, unconnected to any insurance company, available by phone or in person. Find your local SHIP counselor at shiphelp.org, or call 1-800-MEDICARE (1-800-633-4227), available 24 hours a day. If AI ever feels like too much, a SHIP counselor can walk through your specific plan options with you for free.
I already have a Medicare Advantage plan — do I still need to do anything?
It's worth at least checking, even if you're happy with your current plan. Medicare Advantage and Part D plans can change their premiums, drug formularies, and provider networks every year, and your own prescriptions or doctors may have changed too. Your plan should have sent you an Annual Notice of Change letter in September explaining what's different for next year — that's the document worth pasting into AI for a plain-English summary before you decide whether to stay enrolled or switch.
Radim S.
Founder & editor

Radim is a software developer who spends his days building with AI and his evenings explaining it to family members who don’t care how it works — only what it can do for them. The safety guides are checked claim by claim against primary sources before they go out.

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