Flights are more expensive than ever, but I used AI and booked a $1100 international trip for just $365… no credit card points, no shady sites, and no 5-hour layovers in weird cities.
How? I used ChatGPT.
Below are the exact 7 prompts I’ve used, tested, refined, and optimized to help the AI dig up better deals than Google Flights or Expedia ever showed me. Whether you’re a budget traveler or just love hacking the system, these will give you a serious edge.
These are the exact commands that uncovered deals airlines would rather you never find
The AI Flight Hacking Prompts That Actually Work
After testing dozens of prompts, these 7 consistently delivered the best results. These specific commands dig deeper than standard searches and uncover strategies and deals most people never find.
Simply paste in any prompt and replace the bracketed placeholders with your specific details (like [route], [budget], or [city]).
Hidden Deal Finder Prompt
Find the cheapest flights from [departure city] to [destination] around [dates]. Include alternate airports, off-peak days, and creative routes under $300.
Budget Airline Tracker Prompt
List top budget airlines that fly between [City A] and [City B]. Show me how to track their weekly lowest fares using tools or sites.
Flight Price Drop Notifier Prompt
Recommend 3 services that notify me when flight prices for [route] drop below [budget]. Include quick setup steps.
Error Fare Scanner Prompt
Where can I consistently find international flight error fares from [city]? Link me to reliable sources and how to book them fast.
Multi-City Hack Builder Prompt
I want to visit [City 1], [City 2], and [City 3]. Build a cost-efficient multi-city flight route that’s cheaper than booking one-way tickets.
Travel VPN Trick Prompt
Explain step-by-step how to use a VPN to find lower flight prices by region. Use a free VPN as an example.
Carry-On Only Flight Filter Prompt
How can I find the cheapest carry-on only flights for [your route]? Exclude baggage fees and show sites with accurate filters.
*Use these with a free or paid ChatGPT account or Claude.ai, both work equally well for andy of these.
Get More Out of These Prompts!
Don’t treat it like a one-and-done search. Ask follow-up questions to dig deeper! Have a conversation with it.
“What about mid-week flights?”
“Are there cheaper nearby airports?”
“Can you check one-way vs. round-trip pricing?”
“What if I’m flexible with my dates by a few days?”
“Are there any seasonal patterns I should know about?
The AI will respond conversationally and give you more personalized options with a bit of back-and-forth.
The more information you give it about you, your trip, and your preferences, the more helpful it will be.
Once you get useful results, save them or set up the price alerts and tools the AI recommends.
The real savings come from acting on what you discover, not just collecting information.
Tools Mentioned by AI (and Why They’re Useful)
When you run these prompts, certain tools and websites will come up repeatedly. Here are the ones that consistently can up for me and have delivered me results recently:
- Skyscanner – Excellent for multi-city routes and works well with VPN price comparison tricks
- Hopper – Sends reliable price drop alerts and predicts whether to book now or wait
- Google Flights + FlightAware – Best combination for real-time data and flexible date filtering (one of my personal favorites for YEARS)
- Secret Flying / Fly4Free – Specialized sites that catch error fares before airlines fix them
- Momondo – Often finds deals other search engines miss, especially for international routes
- ITA Matrix by Google – Advanced search tool that reveals routing options most sites don’t show
Each of these tools has strengths in different situations, and the AI will often recommend the right combination based on your specific travel needs.
What Actually Worked for Me
- When I first used the “Hidden Deal Finder” prompt, I expected something basic. Instead, ChatGPT recommended switching airports to a smaller hub 40 miles away. That unlocked a $320 round-trip fare from Denver to Barcelona.
The drive to the airport added some complexities to our trip, but I was happy to deal with those to save $400 per ticket for two tickets.
- On another flight I stacked that prompt with a Tuesday departure (thanks to another prompt), and the total savings was over $600.
This was for shoulder season travel booked about 8 weeks in advance. It took 10 minutes of prompting… but worth it.
- The “Multi-City Hack Builder” prompt surprised me too. What seemed like it would be more expensive, visiting three cities instead of one. It actually saved us $512 total compared to booking separate round-trips.
The AI found routing combinations I never would have thought to check.
- Most recently, the “Error Fare Scanner” prompt led me to a business class seat for the price of economy.
The deal lasted maybe 6 hours before the airline caught it, but I’d already booked and confirmed. With error fares, speed matters!
If you see something that looks too good to be true, screenshot it and book immediately if it’s legitimate.
TIP 1: Tuesday and Wednesday departures consistently save money because business travelers avoid mid-week flights.
TIP 2: Smaller airports work because they have less competition and airlines use them to fill planes on less popular routes.
Additional Prompts to Try
Points & Miles Maximizer Prompt
Show me the best ways to use credit card points or airline miles to book a flight from [City A] to [City B]. Include sweet spots and transfer partner tips.
Shoulder Season Saver Prompt
When is the shoulder season for [destination]? Suggest the best weeks to fly there for fewer crowds and cheaper fares.
Hidden City Ticketing Prompt
Explain how hidden city ticketing works with a real example from [City A] to [City B]. What are the risks and best tools to find these fares?
Google Flights Graph Hack Prompt
How do I use the Google Flights price graph to spot the cheapest travel days for a roundtrip from [origin] to [destination]? Give me a 3-step guide.
Red-Eye & Overnight Deal Prompt
Find the best overnight or red-eye flight deals from [departure airport] within the next 60 days. Prioritize under $200 fares.
Mistake Fare Telegram Alert Prompt
What are the top Telegram or Discord channels that send real-time mistake fare alerts? List a few and how to join them.
Flight Deal Email Curator Prompt
Recommend 5 free flight deal email newsletters that specialize in cheap international fares from [nearest major airport]
24-Hour Cancellation Trick Prompt
How can I book a flight now and cancel or change it within 24 hours for free? Which airlines allow this and how does it work?
Midweek Price Dip Prompt
What days of the week are flights from [city] to [city] usually cheapest? Explain how to test this using a flexible calendar tool.
Low-Cost Carrier Bundle Prompt
Which low-cost airlines fly to [destination] from [region]? Show me how to bundle flight + hotel for extra savings under $500.
Hopefully that gives you some additional prompts to try and different thoughts about how to approach using AI with your travel plans.
Risks, Limitations, and Travel Hacking Ethics
These prompts work, but smart travelers know the potential pitfalls and play by the rules.
- Price disappearing at checkout – Some deals vanish when you try to book. Screenshot prices and have backup options ready.
- Hidden fees – Budget airlines especially love adding charges after the initial quote. Read the fine print.
- Error fares aren’t guaranteed – Airlines can cancel tickets bought on obvious pricing mistakes, even after confirmation.
- Don’t game the system – Using fake names, addresses, or payment info can get you banned from airlines permanently.
- VPN risks – Some booking sites detect VPN use and may block your purchase or charge different rates.
Why This Changes Everything
Here’s what most travelers don’t realize: airline pricing algorithms are sophisticated revenue extraction machines, constantly adjusting fares based on demand, competition, and your browsing behavior.
These AI prompts essentially give you the same analytical power that travel agents and corporate booking systems use, but for free.
Once you’ve mastered the basics, you can start combining prompts for compound savings.
Try running the “Hidden Deal Finder” alongside the “Multi-City Hack Builder” for the same trip, or stack the “VPN Trick” with the “Budget Airline Tracker” to compare prices across different regions and carriers.
The AI excels at finding connections between these strategies that human searchers miss.
But don’t stop at flights.
These same prompt techniques work great for:
Hotels – “Find boutique hotels under $150 in [city] with free breakfast and parking”
Car rentals – “Compare one-way car rental costs vs. round-trip for [route] including all fees”
Travel insurance – “Analyze travel insurance options for [trip type] and highlight coverage gaps most policies miss”
5-Minute Challenge
Ok, pick an upcoming trip right now, or pretend you have one coming up, and run just one of these prompts.
Your goal isn’t to book something, it’s finding at least 3 alternatives to whatever flight search you’ve already done.
It’s fun to discover options you never knew existed.
The travel industry has been using AI and automation for years to optimize their revenue.
Now it’s your turn to level the playing field.
The algorithms work for whoever knows how to use them, and now you do.
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