Stop Searching, Start Prompting: The Ultimate Guide on How to Find Cheap Flights with AI

 

Let’s be honest. The thrill of planning a trip is often crushed by the sheer stress of finding the right flight. You open 40 tabs, pitting Google Flights against Skyscanner against Hopper and Kayak. You clear your cookies, used incognito mode with your VPN, convinced the airlines are watching you. Prices change by the minute, and you’re left wondering if you just missed the deal of a lifetime. It feels like you’re playing a game you can’t win. Well, finally, friends, I think we’ve unlocked the best strategy to give you the best advantage by breaking down exactly how to find cheap flights with AI.

For years, airlines have used sophisticated algorithms – what they call “Revenue Management” – to predict exactly how much you’re willing to pay. It’s their AI versus your patience. Well, the game has changed.

It’s time to level the playing field. With the rise of powerful AI chatbots like ChatGPT and Gemini, we can finally fight algorithms with algorithms. This isn’t just about searching faster; it’s about searching smarter. It’s about turning a one-sided conversation into a dialogue where you’re in control, uncovering hidden routes, discovering unlisted airlines, and building the perfect trip on your terms.

Forget the 40-tab chaos. Let’s learn how to prompt.

Fighting AI with AI: Leveling the Playing Field

This feeling of playing a rigged game is more real than ever. In early 2025, major carriers like Delta Air Lines made headlines by announcing strategic partnerships with tech giants like IBM to infuse their operations with next-generation AI. For the everyday traveler, this means the algorithms setting ticket prices are evolving from simply complex to hyper-intelligent. They can now analyze millions of data points in real-time—from local events and weather to your own search patterns—to pinpoint the maximum price you’re willing to pay. And this is the part that seems unfair! This growing information asymmetry is exactly why a new approach to travel hacking with AI isn’t just clever; it’s essential. It’s time to level the playing field. If airlines are using advanced AI, we need to use the same tools to find the deals they’d rather we didn’t see.

Best Practices for Finding Flights with AI

Before you dive in, think of AI as your brilliant-but-new travel assistant. You need to give it good instructions and double-check its work.

• Be Specific and Conversational: The magic is in the details. Don’t just say “cheap flights to Paris.” Say, “I’m looking for a flight from Atlanta to Paris for a 7-day trip in the first two weeks of October. My budget is around $800, and I prefer flights with no more than one stop.” The more detail you give, the better the result.
• Iterate and Refine: Your first prompt is a starting point. If the AI gives you flights that are too expensive, add a budget constraint. If the layovers are too long, tell it to shorten them. Think of it as a conversation to narrow down the perfect option. More thank your personal assistant – it’s your AI personal travel agent!
• Always Verify Before You Buy: This is the most important rule. AI can sometimes “hallucinate” and invent flight numbers or mix up details. Use the AI for discovery, not for booking. Once you find an itinerary you love, take the exact details (airline, flight numbers, dates) and verify them directly on the airline’s official website.
• Book Directly or with Reputable OTAs: Whenever possible, book your flight directly with the airline. It makes handling any changes or cancellations infinitely easier. If you must use an Online Travel Agency (OTA), stick to well-known, reputable ones.
• Keep a “Shortlist”: When the AI spits out a great option, don’t lose it. Copy the details into a simple notes app or spreadsheet. Include the flight info, the price, and the link where you verified it. This helps you compare your top choices without starting over.

The Best AI Prompts for Cheap Flights: Your Travel Hacking with AI Toolkit

Here are the exact prompts I use to find incredible deals and options that regular search engines miss. This is the core of travel hacking with AI; giving the chatbot a better instruction than anyone else. My home airport is ATL, but of course, you’ll adapt these prompts to fit your travel itinerary.

Category 1: Finding the Best Flights

1. The “2-in-1 Trip” Stopover Prompt

• The Prompt: “I want to fly from Atlanta (ATL) to Rome (FCO) in September 2025. Find me options with a layover of at least 12 hours in a major European hub like Amsterdam, Lisbon, or Zurich. My goal is to explore the layover city for a day. Prioritize options that aren’t significantly more expensive than a standard flight.”
• Why it Works: Search engines are designed to find the shortest layover. This prompt forces the AI to do the opposite, unlocking a “two trips in one” experience for a fraction of the cost.

2. The “Reverse Destination” Budget Prompt

• The Prompt: “I have a travel budget of $700 for a round-trip flight from ATL. I want to take a 5-day trip during the first two weeks of October 2025. Give me a list of 5 international destinations I can fly to within this budget. For each one, tell me why it’s a great place to visit that time of year.”
• Why it Works: This flips the script. Instead of choosing a destination and hoping it fits your budget, you give the AI your budget and let it find the destinations for you. You can even refine further by telling it what kind of experience you are looking for – beach, adventure, city vibes. This is a wonderful strategy for discovering your next adventure.

3. The “Best Value & Comfort” Prompt

• The Prompt: “Compare round-trip flights from ATL to LAX for the last week of August 2025. Analyze them not just by price, but by ‘best value.’ Create a table including Price, Airline, Total Travel Time, and Aircraft Type. Flag the top 3 options that offer the best balance of price and comfort (e.g., newer planes like a Boeing 787 or Airbus A350).”
• Why it Works: The cheapest flight isn’t always the best one. This prompt helps you avoid miserable red-eyes on old, cramped planes by factoring in comfort, which is something most search filters ignore. Use SeatGuru as your companion to verify the aircraft, too!

4. The “Alternate Airport” Strategy

• The Prompt: “I want to attend Oktoberfest in Munich in late September 2025. Flights directly into Munich (MUC) are expensive. Find cheaper flight options by searching for airports within a 3-hour train ride of Munich (like Nuremberg, Stuttgart, or Frankfurt). Provide the estimated flight cost and the typical cost and duration of the train journey to Munich.”
• Why it Works: Airlines hike prices to major event cities. This prompt uses logistical intelligence to find a backdoor route that can save you hundreds.

5. The Low-Cost Carrier Discovery Prompt

• The Prompt: “List low-cost carriers that fly from South Florida (MIA or FLL) to Medellin, Colombia, that might not show up on major travel sites like Expedia. I’m looking for a flight in early December 2025.”
• Why it Works: A surprising number of budget airlines don’t pay to be on the big search engines. This prompt specifically asks the AI to find those hidden gems that aggregators miss.

6. The “Split-Ticketing” Combo Prompt (100% Legit)

• The Prompt: “Find me a round-trip flight from ATL to London (LHR) for the first week of November 2025. First, search for it as a standard round-trip booking. Then, search for it as two separate one-way tickets (ATL-LHR and LHR-ATL), even if they are potentially on different airlines. Compare the total cost and show me the cheapest combination.”
• Why it Works: Sometimes airline pricing logic results in two one-way tickets being cheaper than a round-trip. This is tedious to check manually but effortless for an AI. And if you’re loyal to one airline group, you can include in the prompt to stick with journeys that stay within those restrictions.

Category 2: Beyond Flights: Using an AI Travel Planner for Hotels & Itineraries

Now that you’ve got the hang of using your AI personal travel agent, you’ll realize that it isn’t just for flights. Use the same logic to plan the rest of your trip. Remembering the best practices I gave you at the top of this post, be sure to give additional prompts and request it to deep research when necessary to make sure the recommendations go beyond the “top SEO” written about posts, blogs and sponsored content.

• For the Perfect Hotel: “Find me a boutique hotel in the Le Marais district of Paris for 4 nights in October. My budget is under $350/night. It needs to have character, be highly rated for cleanliness, have air conditioning, and be within a 5-minute walk of a Metro station. Do not include large international chains like Marriott or Hilton.”
• For Building an Itinerary: “Create a 4-day walking-focused itinerary for a first-time visitor to Lisbon, Portugal. Group activities by neighborhood for each day to minimize travel time. The themes are ‘history and food.’ Include a mix of major landmarks and local food experiences.”
• For On-the-Ground Logistics: “I land at London Heathrow (LHR) at 8 AM on a Wednesday. My hotel is near Paddington Station. What are all my transportation options? Compare the Heathrow Express, the Tube, and an Uber based on cost, total travel time, and convenience for someone with one large suitcase.”

Bonus 1: Supercharge ChatGPT for Flight Booking with Custom Instructions

While you can’t entirely use AI instead of Google Flights for real-time price alerts, you can make the process infinitely faster by teaching it who you are. The “Custom Instructions” feature in ChatGPT for flight booking pre-loads your preferences into every conversation.

How to Set It Up:

1. In ChatGPT, click your name, then select “Custom Instructions.”
2. You’ll see two boxes. In the first box, “What would you like ChatGPT to know about you to provide better responses?”, paste this:My home airport is Hartsfield-Jackson Atlanta International Airport (ATL). I am based in Atlanta, Georgia. I primarily fly Delta but am open to other airlines if the deal is good. I have loyalty status with Delta (SkyMiles) and Hilton (Honors). I prefer non-stop flights but will consider one-stop options for significant cost savings.
3. In the second box, “How would you like ChatGPT to respond?”, paste this:Act as an expert travel assistant. When presenting flight or hotel options, use a table format for easy comparison. Always state prices in USD. Prioritize value, which is a balance of cost, convenience, and comfort. When suggesting an itinerary, group activities geographically to make it efficient.

Now, every time you start a new search, the AI already knows your home base and preferences. You can just ask, “Find me the best value flight to LAX next month,” and it will handle the rest.

Bonus 2: Put Your Flight Search on Autopilot with ChatGPT Tasks

Ready for the ultimate pro-level tip? The real secret to effortlessly staying on top of flight deals is to make the AI do the work for you, even when you’re not online. Using a powerful built-in feature called Tasks, you can turn ChatGPT into your personal, automated flight tracker.

Imagine setting up a search once and getting the best flight deals for your dream trip emailed to you every single week. Here’s exactly how to do it.

How to Set Up a Weekly Flight Search Task:

1. Select the Right Model

First, make sure you’re using a model that supports Tasks. At the top of the screen, select o3 or o4-mini from the dropdown menu.

2. Give ChatGPT Your Automated Prompt

Next, you simply ask ChatGPT to create the task for you in plain English. For the best results, be as specific as possible with your flight details, the schedule, and how you want to receive the information.

Here is an example prompt you can adapt:

“Create a recurring task for me. Every Friday at 9:00 AM, search for the best value round-trip flights from ATL to Lisbon, Portugal (LIS) for a 7-day trip anytime in October 2025. Analyze price, airline, and total travel time, then email me a list of the top 3 options you find.”

3. Confirm the Task

Once you submit your prompt, ChatGPT will show you a confirmation of the task it’s about to create. It will outline the action, the schedule, and the delivery method. Simply confirm it, and you’re all set.

4. Check Your Notification Settings

To make sure you get the results, double-check that your email notifications are enabled. You can manage this in your Notifications settings on the ChatGPT website.

That’s it. Your AI travel assistant will now search for flights and report back to you every week without you having to lift a finger. This is the ultimate way to use AI instead of Google Flights for tracking deals over time, ensuring you never miss an opportunity to book when the price is right.

 

The secret to how to find cheap flights with AI isn’t about having access to a secret website; it’s about asking better questions. This is more than just a new way to search. It’s about taking back control and making travel planning fun again.

What’s the best deal you’ve found using AI? Share your favorite prompts in the comments below!