Shopping for health insurance is overwhelming, even for people who work in the industry. Between confusing plan names, network fine print, and pages of cost-sharing rules, it’s easy to miss the details that actually matter for your family.
If you’re using an Individual Coverage HRA (ICHRA) from your employer, it gets even trickier because you’re balancing your monthly allowance with the Marketplace options.
The good news? AI tools like ChatGPT can make this process a lot easier if you know how to use it. Here are some practical ways, even if you’re brand new to ChatGPT or ICHRA, to simplify and organize your plan selection.
Important note before we get started: ChatGPT is not HIPAA-compliant, meaning you should not share protected health information (PHI) with the platform. Stick to general details like your zip code, age, plan names, and shorthand for common medications and stay away from sharing things like social security numbers, medical record numbers, or detailed clinical notes.
Alright, let’s get to it!
1. Share Your Health Insurance “Shopping Packet”
One of the most powerful parts of ChatGPT is its ability to maintain context throughout your conversation with it (if you’re logged in). Before you start, give ChatGPT the basics to establish your baselines:
- ZIP code + county
- Ages of everyone applying
- Monthly ICHRA allowance (if you have one)
- Any must-have doctors or hospitals
- Your top medications
- Budget or cash flow needs
- Preference for HSA-eligible plans (yes/no)
This helps ChatGPT screen plans with your real-world needs in mind, not just the headline premium.
2. Extract and Standardize Health Plan Details
SBCs (Summary of Benefits and Coverage) are how health insurers have to standardize how they explain the structure of any given health plan and boy are they long and confusing. You can paste text from them into ChatGPT or even upload the whole thing and ask:
“Can you make a clean table of the deductible, out-of-pocket maximum, PCP/specialist costs, Rx tiers, referral rules, and telehealth?”
This makes it much easier to compare plans side by side.
3. Estimate Yearly Health Insurance Costs
Premium isn’t the full story. Share a quick estimate of your healthcare use (e.g., 3 PCP visits, 2 specialists, 1 brand-name prescription). Then ask:
“What’s my total expected annual cost = (premium – allowance) + out-of-pocket spending?”
You can also ask for a healthy year scenario, an average use case scenario and a worst-case year (when you hit your out-of-pocket ma\
4. Find Break-Even Points
Sometimes a Bronze plan looks cheap until you need care. An example prompt:
“At what point (number of visits or prescriptions) does Plan A become more expensive than Plan B?”
This helps you see trade-offs in plain English.
5. Double-Check Your Health Plan Network
Paste the names of your doctors and hospitals and ask ChatGPT to make a checklist against each plan. It won’t replace the official directory, but it helps you stay organized and spot obvious mismatches.
To be positive that your doctors are in network, we always recommend that you reach out directly to them to double check that they’ll accept your finalized plans.
6. Simplify Prescription Coverage
List your top medications and ask for a table showing likely tiers, copays/coinsurance, and any special restrictions (like prior authorization). This gives you a quick snapshot of what to confirm with each carrier. (FYI: Prior authorization is when a doctor has to ask your health insurance company for permission before a medicine, test, or treatment is covered.
7. HSA Eligibility Watch
If you want to use a Health Savings Account (HSA), ask ChatGPT to flag “gotchas” like pre-deductible copays or embedded family deductibles. These small details can make or break HSA eligibility.
8. Optimize for ICHRA
Tell ChatGPT your allowance amount and have it sort plans by:
- Lowest monthly cost after the allowance
- Lowest worst-case total annual cost
This makes the trade-offs crystal clear.
9. Plan for Travel or College Kids
If a dependent spends time out of state, ask:
“Which plans only cover out-of-area emergencies, and what are the alternatives?”
You’ll avoid surprises with HMOs or EPOs that don’t travel well.
Note: all plans will have you covered at in-network rates in the event of an emergency but if you do intend to spend a lot of time out of state, it’s important to ensure that you’ll still have access to basic healthcare as well.
10. Spot the Hidden Gotchas
Ask ChatGPT for a “gotcha scan” of the plan—things like referral rules, therapy visit caps, or prior auth requirements. It won’t catch everything, but it will flag common pain points.
11. Keep a Decision Log
Once you’ve chosen a plan, have ChatGPT write up a one-page memo: what you picked, why, and what assumptions you made. Next year, you’ll thank yourself for leaving a paper trail - plus you can feed this back into ChatGPT along with your experience with your plan to accelerate this process next year.
Guardrails
- Don’t paste sensitive personal identifiers or sensitive information into ChatGPT.
- Always verify provider networks and drug tiers directly with the health insurance carrier before enrolling.
- If you’re eligible for subsidies on Healthcare.gov, remember you can’t combine them with ICHRA. More detail on subsidies (AKA premium tax credits) can be found here.
Bottom Line
Choosing an ACA plan is stressful, but ChatGPT can act like your personal organizer: extracting details, running cost scenarios, and surfacing the fine print. Paired with your ICHRA allowance, it turns a messy, high-stakes decision into something manageable.
