ChatGPT: Delays, refunds & claims

Win hotel and airline refunds after a medical trip cancellation with ChatGPT

A Reddit user had to cancel a trip to Medellín, Colombia, at the last minute because of a sudden medical emergency, and the hotel and airline both refused refunds. The traveler told ChatGPT about a generalized anxiety disorder diagnosis backed by a doctor's note, and it read the policies of the airline, the hotel and Expedia and drafted a refund letter. The hotel agreed to a refund. The airline said it only refunded 'due to death or terminal illness', so ChatGPT wrote a second letter on how the condition affected flying, and an hour after it was sent, the airline changed its mind. The traveler says ChatGPT saved about $2,500.

Get a $500 trip delay claim paid without receipts with a letter drafted by ChatGPT

Michelle got home 24 hours late after a snowstorm delayed a connection in Dallas: a night with friends, another full day at the airport, and a rerouted flight to a city about two hours from home. A Chase Sapphire Reserve card turned out to include trip delay insurance, but the claim wanted receipts and Michelle had none. Michelle told ChatGPT exactly what happened; it said the claim was worth a try, helped write a letter explaining everything, said to include the boarding pass and flight details, and showed where to submit it. A week later the claim was approved for $500, the maximum benefit, and the check arrived.

Win a Lufthansa refund for a cancelled trip over months of ChatGPT-written emails

After a Lisbon–Frankfurt–Miami flight was delayed, boarded and then cancelled, the poster gave up the trip and flew elsewhere. Lufthansa tried to charge for the Lisbon–Frankfurt leg and offered only 'the difference'. The poster fought it entirely by email using ChatGPT, and after months and a long chain of emails got the refund. They still lost money, days and the trip with their mother.

Untangle codeshare delay compensation across three jurisdictions with ChatGPT

When a delay turned a 2-hour layover into an overnight stay in Turkey, a traveller first used ChatGPT to translate their correspondence for a Turkish-only support portal, then got the runaround: two airlines, a codeshare, three jurisdictions, and compensation firms that turned them down. Once they explained the full situation, they say ChatGPT reasoned through the rules, told them which airline to chase and what to say, and that airline agreed to compensation; they say they got $500.

Claim compensation for a long flight delay (EU261) with ChatGPT

After a Norse Atlantic flight from Oslo was delayed overnight and the airline offered a $25 refreshment card, then ignored their claims, the author pasted the delay email into ChatGPT Pro and asked about their rights. Over eleven months it walked them through EU261 (600 euros per passenger for four people), the national complaint body, the Norwegian conciliation court and a settlement including statutory interest; on July 14, 2026, the airline wired $4,760.36.

Poster says:$4,760.36 paid after eleven months