← Blog · 2026-10-19 · 7 min read

Use AI to compare health plans at open enrollment

What it does for you: if a stack of plan papers is sitting on your table right now, this turns it into a simple side-by-side: what each plan would really cost you in a quiet year and a rough year, whether your doctors and medicines are covered, and a short list of questions to ask before you pick. AI does the reading and the math. You, the plan's own documents, and a free counselor make the decision.

It's that time of year. Medicare Open Enrollment runs October 15 to December 7 (Medicare.gov). Marketplace (HealthCare.gov) enrollment for 2027 opens November 1 and, in most states, runs to January 15, with December 15 the last day for coverage that starts January 1 (HealthCare.gov). Many jobs run their benefits enrollment in the fall too, with their own dates.

And people are stuck. This week on X, one parent called adding a stepson to next year's insurance "so confusing." On Reddit, someone whose spouse is in remission said they were scared of picking the wrong plan. That fear is fair. Plans change every year, and the cheapest monthly price is often not the cheapest year.

Before you start: strip out the private stuff

Never paste your Medicare number, Social Security number, member ID, date of birth, or bank details into any chatbot. You don't need them for any step here. Use the plan names, the costs, and your list of medicines and doctors. That's enough.

If you use ChatGPT, a Temporary Chat stays out of your history and isn't used to train OpenAI's models, though OpenAI may keep a copy for up to 30 days for safety (OpenAI Help). Gemini, Claude, and Copilot all work for this too; just leave out the same details.

Step 1: Gather the right papers (10 minutes)

• Medicare: the Annual Notice of Change letter your plan sent in September. It lists what's changing for 2027 (Your Yearly Medicare Review, PDF).
• Job or Marketplace plans: the Summary of Benefits and Coverage for each plan you're considering. It's a standard form, so plans are easy to line up.
• Your own list: your medicines and doses, the doctors you want to keep, your pharmacy, and roughly how often you saw a doctor this year.

Most of these come as PDFs you can upload, or you can copy the text of the first two pages.

Step 2: Decode the letter (2 minutes)

Upload or paste your Annual Notice of Change, or one plan summary, and ask:

The "quote the exact line" part matters. It lets you check every number against the paper in seconds. For more practice with confusing mail, try the free drill Decode a confusing letter or bill in plain English.

Step 3: Compare the real yearly cost (5 minutes)

HealthCare.gov's advice is to compare your total yearly cost, not just the premium: premiums for the year, plus what you pay when you get care, up to the out-of-pocket maximum (HealthCare.gov). AI is good at running that math three ways:

A quick sanity check on the math: the rough-year number for each plan should be about a year of premiums plus that plan's out-of-pocket maximum. If the AI's table doesn't match that, ask it to redo the math. Paid per paycheck at work? Give it the per-paycheck amount and how many paychecks you get a year.

Step 4: Check your doctors and medicines (the step that matters most)

A cheap plan that drops your doctor or your medicine isn't cheap. AI can't see a plan's current network or drug list, so don't ask it whether your doctor is in network. Use it to build your checklist instead:

Then do the lookups on the real tools:

• Medicare: the Medicare Plan Finder compares plans side by side using your drugs and pharmacy, and shows estimated total costs and star ratings.
• Marketplace: HealthCare.gov (or your state's own site, like Pennie in Pennsylvania or Covered California) once enrollment opens November 1.
• Work plans: your benefits portal, or call the plan's member number on the summary.

Step 5: Get your questions ready for a person (2 minutes)

For Medicare, the best person to ask is free: your local State Health Insurance Assistance Program (SHIP) gives unbiased counseling and can walk you through the Plan Finder. Find yours at shiphelp.org, or call 1-800-MEDICARE (1-800-633-4227), which answers around the clock (Medicare.gov).

Common mistakes

• Picking by premium alone. The lowest monthly price can be the most expensive plan in a rough year.
• Doing nothing without checking. If you're happy with your Medicare plan you don't have to act, and it continues automatically. But its costs and drug list can still change on January 1, so read the notice first.
• Trusting an AI answer about networks or drug lists. That changes plan by plan and year by year. Check the plan's own tools.
• Giving your info to a caller. Medicare won't call to sell you a plan or ask for your Medicare number out of the blue. Hang up and call 1-800-MEDICARE yourself (FTC).

Honest limits

• AI can misread a number. That's why every prompt asks it to quote the document and show its math. Check anything you'll base the decision on.
• It isn't advice. AI doesn't know your full health picture, and it isn't licensed. Use it to understand the papers and prepare, then decide with the official tools or a counselor.
• Dates differ. Some states run their own Marketplace with different deadlines, and every employer sets its own window. Confirm yours.
• Free vs paid: every step works on free plans of ChatGPT, Gemini, Claude, or Copilot. Free plans may limit how many files you can upload in a day; pasting the text of the first two pages works just as well.

Your 15-minute challenge: find one plan letter or summary in your mail or email today and run the Step 2 prompt on it. You'll know what's changing before the deadline sneaks up.

If budgeting is next on your list, the free drill Build a budget around your paydays pairs well with this. More free drills are on the Drills page, and the Life Scripts Starter pack ($9 founder price) has 40 copy-paste scripts for everyday paperwork, planning, and checking whether an AI answer holds up.

Sources

• Medicare.gov: Open Enrollment (October 15 to December 7, changes start January 1)
• Medicare.gov: Your Yearly Medicare Review (PDF) (Annual Notice of Change, Plan Finder, SHIP, 1-800-MEDICARE)
• Medicare.gov: Medicare Plan Finder
• SHIP: shiphelp.org (free local Medicare counseling)
• HealthCare.gov: Dates and deadlines for 2027 coverage
• HealthCare.gov: Your total costs for health care
• HealthCare.gov: Glossary of health coverage terms (deductible, out-of-pocket limit)
• healthinsurance.org: ACA open enrollment dates by state
• FTC: Protect yourself from scams this Medicare Open Enrollment
• OpenAI Help: Temporary chat in ChatGPT