Search for cheap flights with ChatGPT agent (failure case)

Posted

Aug 20, 2025 by Max Drescher (@maxdrescher_)

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Last checked

Oct 16, 2026

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Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

ChatGPT agent suggested flights costing $1,400 when the poster found an $850 option on their own.

Agent

ChatGPT agent

Strengthened by us to avoid the problem in the source. Not tested by the poster. It doesn't change what happened in the source.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Find the cheapest real flights for my trip and show me how you know they're the cheapest.

Check with me first: Where from and to, which dates, and how flexible am I?

What I'll give you:
- From [CITY/AIRPORT] to [CITY/AIRPORT]
- Dates [DATES] and flexibility (e.g. ±2 days)
- Number of travellers and bags
- Any airlines or stops to avoid

Rules:
- Search at least two sources (for example Google Flights and Skyscanner) and include nearby airports and ±[N] days if I'm flexible.
- Compare total prices including bags for the same number of travellers.
- Before listing a fare, open it and confirm it's still available at that price.
- Tell me the cheapest option you found and how much it beats the next one by. If something looks too expensive, keep searching rather than settling.
- Don't book or pay. Hand the final choice to me with the link.

Output: A short table of the 3 cheapest options with airline, times, stops, total price, the source and a working link.

If anything here is unclear or missing, ask me instead of guessing.

You'll know it worked when: I've seen the cheapest fare across sources, and I can open it at the price listed.

Find me the cheapest flights for this trip.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Find the genuinely cheapest flights for my trip and prove they're the cheapest.

Quick check first: tell me if anything below is missing or unclear.

Inputs (fill in or confirm):
- From and to
- Dates and flexibility
- Travellers and bags
- Airlines or alliances to prefer or avoid
- How I'll know a fare is real (shown on airline or OTA booking page)

Rules:
- Search at least three sources, including the airline sites and a metasearch.
- Check nearby airports and ±flex dates.
- Include bag fees in totals.
- Show the cheapest found on each source.
- Check one-way combinations and separate airlines, but flag self-transfer risks.
- Note fare conditions (bags, changes, refunds) next to each price.
- Use a private window or clear cookies if prices seem to rise on repeat searches.

What went wrong before, and how to avoid it:
- Last time it suggested a $1,400 flight while an $850 option existed: compare multiple sources and report the cheapest from each.

Checkpoint: Don't book.

If you get stuck: If a site blocks you, say so and continue with others. If a login, CAPTCHA or two-step code appears, stop and ask me to handle it; never guess or store passwords.

Verify before you finish: Re-open the top option to confirm price.

Output: Table of options with sources.

Done when: I have the cheapest verified fare.

Source

https://x.com/maxdrescher_/status/1958253813770674556