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AI Battle of the Week

ChatGPT vs Claude for one real task: checking a confusing medical bill and drafting a dispute letter.

No made-up benchmarks. We haven't found an independent, like-for-like test of these two on bill disputes. So this compares features and pricing from each official pricing page (checked 2026-10-13) and links to real people who used each one.

For this task	ChatGPT	Claude
Free plan	Yes. Unlimited everyday text chats (abuse guardrails apply).	Yes, $0. Usage limits reset every five hours.
Uploading your bill on the free plan	Limited file uploads and limited vision (reading images).	Not stated on the pricing page. It lists chat, web search, file creation and code execution.
Deep research for rules and rates	Limited on Free; expanded on Plus.	"Research" is not on Free; it starts on Pro.
Models on the free plan	GPT-6 Luna (per the plan table).	Sonnet and Haiku; Opus needs Pro.
Cheapest paid plan	Go. The price isn't in the page text we fetched, so check the page.	Pro: $20/month, or $17/month billed annually ($200 up front).
Real-world example on this site	Jamie Phillis used ChatGPT to find bad charges on a dental bill and draft appeals. She never paid the $1,200.	Matt Rosenberg used Claude to compare a $195,628 hospital bill with Medicare rates and settled at about $32,500. He checked the work with ChatGPT.

Our take

Both free plans can explain a bill and draft a letter. The differences that matter here are file uploads, research features and usage limits.
The people in both stories checked the AI's work: one ran it through a second AI and read the Medicare rules himself. Whichever you pick, do the same.
Want the steps? Copy the hospital bill play or the dental bill play.

Sources

Plans and prices change; check the official pages before you buy. Not sponsored by either company.

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