Compare Health Insurance Plans During Open Enrollment with Free AI

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It’s open enrollment season, the once-a-year window to pick or change your health insurance. And every plan comes with a pile of confusing words: deductibles, coinsurance, out-of-pocket maximums. It’s enough to make anyone pick the same plan as last year and hope for the best. (No judgment. We’ve all done it.)

Good news: a free AI chatbot can help. It can explain the jargon in plain English, line up your choices side by side, and estimate what each plan could cost you in a real year. You still make the choice. The AI just helps you see it clearly.

Step 1: Gather the plan details

First, find the plans you can choose from. Where you look depends on how you get insurance:

• Through your job: Check your benefits website or ask HR. Look for each plan’s Summary of Benefits and Coverage, a short, standard document that health plans have to give you. It lists the key costs in the same format for every plan, which makes comparing easier.
• On the Marketplace: You can preview plans and prices on HealthCare.gov before open enrollment starts, without signing up.
• On Medicare: Use Medicare’s Plan Finder. If you already have a plan, also look for its Annual Notice of Change, a letter your plan sends each fall listing what’s changing next year.

For each plan, write down (or copy) the key numbers: the monthly cost, the deductible, what a doctor visit costs, what your prescriptions cost, and the out-of-pocket maximum. Don’t worry if those words mean nothing yet. That’s Step 2.

Step 2: Get the jargon in plain English

Insurance has its own language. Here’s a quick cheat sheet:

• Premium: what you pay every month just to have the insurance, even if you never see a doctor.
• Deductible: what you pay for care yourself each year before the plan starts paying its share. (Many plans cover some things, like yearly checkups, even before you hit it.)
• Copay: a flat fee for a visit or prescription, like $30.
• Coinsurance: your share of the bill as a percentage, like 20%, usually after you’ve met your deductible.
• Out-of-pocket maximum: the most you’d pay for covered, in-network care in a year. After that, the plan pays 100%. Your monthly premiums don’t count toward it.
• Network: the doctors, hospitals, and pharmacies that have a deal with the plan. Going “out of network” usually costs a lot more.

Seeing a word that isn’t on the list? Medicare uses a few extra terms, like “Part D” (drug coverage) and “Medicare Advantage.” Copy this prompt and fill in any words that confuse you:

I'm choosing a health insurance plan and some of the words confuse me.
Please explain these in plain English, like you're talking to a friend: [list the words, like deductible, coinsurance, formulary].
For each one, give a simple example with dollar amounts.
Keep it short.

Step 3: Line up your plans side by side

Now let the AI build a comparison table. Type in each plan’s numbers, or copy and paste the text from its summary. Leave out anything with your name, member ID, or other personal details.

Please put these health plans side by side in a simple table.
Rows: monthly premium, total premiums for the year, deductible, doctor visit cost, specialist visit cost, generic drug cost, emergency room cost, and out-of-pocket maximum.
Then explain the biggest differences in plain English.
Only use the numbers I give you. If something is missing, write "not listed" instead of guessing.

Plan A: [paste or type the details]
Plan B: [paste or type the details]
Plan C (optional): [paste or type the details]

That last instruction matters. When a chatbot doesn’t have a number, it will sometimes fill the gap with a confident-sounding guess. Telling it not to guess helps keep the table honest.

Step 4: Play “what if” with a quiet year and a rough year

Here’s the big secret of open enrollment: the plan with the cheapest monthly price isn’t always the cheapest plan. It depends on how much care you end up needing. Look at these two made-up plans:

	Plan A	Plan B
Monthly premium	$150	$60
Deductible	$500	$3,000
Out-of-pocket maximum	$3,000	$7,000
Quiet year (premiums only, plus a little for a checkup or two)	About $1,800	About $720
Rough year (premiums plus hitting the out-of-pocket maximum)	About $4,800	About $7,720

In a quiet year, Plan B saves you about $1,000. In a rough year, like a surgery or a hospital stay, Plan A saves you almost $3,000. Neither one is “right.” It depends on your health, your budget, and how much risk you’re comfortable with.

Ask the AI to run the numbers for your plans:

Using the plans in the table, estimate my total cost for one year (premiums plus what I'd pay for care) in three situations:
1. A quiet year: [for example, one checkup and two sick visits]
2. A typical year for me: [describe it, like 6 doctor visits, 2 specialist visits, and one generic prescription every month]
3. A rough year: a hospital stay or surgery where I reach the out-of-pocket maximum.
Show your math step by step for each plan.
Then tell me which plan costs the least in each situation.

Chatbots are great at explaining but can still slip up on simple math. Check the big totals yourself with your phone’s calculator. It takes a minute and could save you hundreds.

Step 5: Check your doctors and prescriptions (don’t trust the AI on this one)

A cheap plan isn’t a deal if your favorite doctor isn’t in it. AI chatbots don’t reliably know which doctors are in a plan’s network or which drugs a plan will cover next year, and those lists change. So check with the real sources:

• Doctors: Use the plan’s online “find a doctor” tool, then call your doctor’s office to confirm. Office staff hear this question all the time.
• Prescriptions: Look up each drug on the plan’s drug list (sometimes called a “formulary”). On Medicare’s Plan Finder, add your drugs and pharmacy to see estimated yearly costs for each plan.

Nervous about making the call? Have the AI write you a script:

Write me a short, polite script for calling my doctor's office.
I want to ask if they will accept [insurance company and exact plan name] next year.
Include 3 questions to ask, and a spot to write down the name of the person I talked to and the date.

Step 6: Make a question list, then get free help from a real person

Before you decide, have the AI turn everything into a short to-do list of questions:

Based on everything we talked about, make a short checklist of questions I should ask [HR / the insurance company / a Medicare counselor] before I choose a plan.
Put the most important questions first.

Then take your list to a real person. This help is free and isn’t trying to sell you anything:

• Medicare: Your local State Health Insurance Assistance Program (SHIP) gives free, one-on-one Medicare counseling. Find yours at shiphelp.org, or call 1-800-MEDICARE (1-800-633-4227).
• Marketplace: Find free, trained helpers near you at localhelp.healthcare.gov.
• Job-based insurance: Your HR or benefits team can answer questions about your company’s plans.

Finally, pick your plan and enroll before the deadline. If you do nothing, many plans simply renew for next year, but the prices and coverage can change. That’s exactly why it pays to take a look.

Try this next

Once you’ve picked a plan, our guide to getting ready for a doctor’s visit with free AI helps you make the most of your appointments. And if a confusing bill or insurance letter shows up later, here’s how to get AI to explain it in plain English.

Common questions