The flight sites show you the price they WANT you to pay. These seven AI prompts — free to use with ChatGPT, Claude or any AI assistant — dig up the routes, the days and the fares the sites keep buried. Copy each prompt exactly as written, swap in your cities and dates where you see the brackets, and let the AI do the hunting.
1. The Hidden Route Finder
“Act as a flight hacker. I need to fly from [CITY] to [CITY] around [DATES]. Find me the routes the big sites don’t show first: hidden-city stops, split tickets and nearby-airport combos. List every option with the airline, the total price, and the catch I need to know before I book.”
Best when your dates can flex a day or two. The “catch” line matters — hidden-city tickets only work if you travel with a carry-on.
2. The Cookie Price Check
“Airlines watch your searches and prices can creep up when you keep looking. Give me a step-by-step plan to check this same flight like a first-time buyer: private window, cookies cleared, a different device, a VPN. Tell me exactly what to compare so I know the real lowest price.”
Run this before you book anything you’ve searched more than twice.
3. The Country Price Swap
“The same seat can cost less when it’s priced for another country. Show me how to compare this flight — [ROUTE + DATE] — on the airline’s sites for different countries, how to pay safely in another currency, and how to check the final total after conversion fees so I don’t get tricked.”
Works best on international routes. Always compare the converted final total, never the sticker price.
4. The Best-Day Finder
“Act as a fare analyst. For flights from [CITY] to [CITY], tell me which days of the week and which weeks are usually the cheapest, how far ahead I should book, and which days to avoid completely. Build me a simple booking calendar for the next 60 days.”
Midweek departures win more often than weekends — let the AI prove it for YOUR route before you lock dates.
5. The Fare Rules Decoder
“Here is the fare I’m about to buy: [PASTE THE FARE DETAILS]. Read the fine print for me like a friend. Is a carry-on included? What happens if I miss the flight, change the date, or need a refund? Plain English only: is this cheap ticket a real deal or a trap?”
The cheapest fare is often cheap for a reason. Sixty seconds with this prompt can save you a $200 surprise at the gate.
6. Airline vs Travel Site Showdown
“Compare this flight — [ROUTE + DATES] — booked direct with the airline versus the big travel sites. Show me the REAL total for each after bags, seats and fees, and tell me which one protects me better if the flight gets cancelled or changed. Pick a winner and tell me why.”
The headline price is never the real price. Make the AI add up bags, seats and fees before you choose.
7. The Price Drop Watcher
“Build me a price-watch plan for [ROUTE] around [DATES]. Which apps and alerts do I turn on? How often do I check? What price counts as a ‘book it NOW’ deal on this route? And if the price drops AFTER I buy, what’s my exact move to get the difference back?”
Set the alerts the same day you start planning — and yes, many airlines will credit you if the price drops after you book. This prompt tells you how to ask.
A cheaper flight feels good. Making the money so the price don’t matter feels better — build the business, then fly whenever you want. Want all seven prompts in one place? They’re on the FreddyO Instagram page too — comment FLIGHTS and we’ll send them to you.
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