Use AI to Compare Health Insurance Plans This Open Enrollment

Before you read on

This is not insurance, medical, legal or financial advice. AI is not an insurance agent or a benefits expert. It can misread a table, mix up two plans, or state something confidently that isn't in your documents. Use it to get ready for the decision, then confirm the details with the plan itself, HealthCare.gov or your state's marketplace, your employer's HR or benefits team, or a licensed broker or navigator. Rules, prices and deadlines vary by state and by employer.

Protect your private information. Don't paste your Social Security number, member ID, policy numbers, date of birth or detailed medical records into an AI tool. You don't need them. Describe your needs in general terms instead, like "two kids, a few doctor visits a year, one monthly prescription." Before uploading a plan document, delete anything personal, and check your AI tool's data settings. If you're not sure something is safe to share, leave it out.

Open enrollment is a big decision made in a hurry

Open enrollment comes once a year. You get a stack of plan options full of words like coinsurance and formulary, and a deadline. Many of us pick the plan we had last year, or the one with the lowest monthly price, and hope it works out.

For HealthCare.gov plans, open enrollment for 2027 coverage runs November 1, 2026 through January 15, 2027, and you need to sign up by December 15 for coverage that starts January 1 (HealthCare.gov). Some states run their own marketplace with different dates, and employer plans set their own windows, so check yours. These dates were current in late October 2026. This post is about marketplace and employer plans; Medicare has its own enrollment period and rules.

AI can't choose for you. But it's good at the first pass: explaining the terms, lining up the options and doing the math.

What AI can help you do

• Explain the jargon. Premium, deductible, copay, coinsurance, out-of-pocket maximum, network and formulary, in plain English with simple examples.
• Summarize a plan. Every plan has a Summary of Benefits and Coverage (SBC), a standard short document. AI can turn one into a few clear paragraphs.
• Compare plans side by side. Put two or three plans in one simple table: monthly cost, deductible, out-of-pocket max, and what common visits cost.
• Estimate your total yearly cost. Monthly premiums plus what you'd likely pay for care, under a few "what if" scenarios: a healthy year, a typical year and a rough year.
• List what to verify. Which of your doctors, hospitals and prescriptions you need to confirm are covered. (AI can't know this for sure. The plan's own directory and drug list can.)
• Write your questions. A short list to bring to HR, a broker or a marketplace navigator.

Try it this week

Download the Summary of Benefits and Coverage for two or three plans you're considering. Delete anything personal. Upload them to a free tool like ChatGPT, Claude, Gemini or Copilot and try this:

Compare these health plans in a simple table: monthly premium, deductible, out-of-pocket maximum, and what I'd pay for a primary care visit, a specialist visit, urgent care, the ER and generic prescriptions. Explain any terms in plain English. For each number, tell me which page or section it came from.

Then follow up with:

Estimate my total yearly cost under each plan for three scenarios: a light year (two checkups), a typical year (about six visits and one monthly generic prescription), and a bad year (a hospital stay). Show your math. Then list the questions I should ask HR or a broker before I choose.

Change the scenarios to fit your own household.

Check its work

This step matters most. AI can misread insurance tables, swap numbers between plans, or mix up "in-network" and "out-of-network" costs.

• Check every number against the plan documents yourself, using the page or section it points to.
• Check the math on the yearly cost estimates. A wrong deductible changes everything.
• Check your doctors and drugs in the plan's own provider directory and drug list (formulary), or by calling the plan. Don't trust AI on who's in network.

Treat the AI like a sharp assistant who sometimes gets things wrong, not the final word.

Where this helps at home and at work

• At home: choosing a marketplace plan, comparing your employer's options with a spouse's, or helping a parent understand their choices.
• At work: helping employees understand their benefits options, and preparing clear questions for your broker before renewal.

Where it gets harder

One person comparing plans once is easy. The harder part is helping a whole team do it well: what's safe to share with AI tools, a simple comparison checklist your people can trust, and knowing when a question belongs with HR or a licensed broker. That's the part we help with.