15 AI Prompts to Save Money When Booking Travel
As a professional travel blogger, I’ve always been good at finding deals on trips. But it was never easy.
Flights, hotels, activities - there are SO many travel apps and tools out there, which made finding deals overwhelming.
Then I started using AI to plan and book smarter. Now I can uncover hidden discounts, time bookings for the cheapest rates, and even get better upgrades without spending hours in browser tabs. These 15 prompts have saved me thousands on travel this past year alone. With GPT-5 and Gemini 2.5, it’s truly never been easier.
If you’re planning a weekend getaway or a multi-country adventure, these prompts can help you stretch your budget and upgrade your experience…without cutting the fun.
NOTE: Each of the prompts below are simply examples. Feel free to replace destination names and other details depending on your specific circumstances.
✈️ Prompt #1: Find the Cheapest Time to Fly
🧠 Prompt to use:
"Find the cheapest dates to fly round-trip from Boston to Barcelona in the next 6 months. Include price history for the past 3 years, predicted trends for the next 90 days, and at least 3 alternative travel windows that are 20% or more below the average. Also suggest if adjusting the trip length by 1–3 days would lower the fare further."
💡 What it does:
Instead of just looking at a static fare chart, this prompt gives you a forward-looking view based on both history and predictions. You can instantly see whether to book now or wait. And sometimes shifting your departure by even one day can mean huge savings.
💥 What I learned:
On a Barcelona trip, I shifted my departure from a Thursday to a Tuesday and saved $312 round-trip. It felt like finding money I didn’t know I had.
🛠️ Tool I used:
I used Google Flights to pull a price graph, then fed that into ChatGPT for analysis. The AI helped me pinpoint “sweet spot” weeks I wouldn’t have guessed were cheapest.
🏨 Prompt #2: Spot Hotel Price Drops
🧠 Prompt to use:
"Track the rates for these 3 hotels in Rome for the next 30 days. Alert me if the price drops by 15% or more from today’s rate. Also, check if booking directly through the hotel website offers extra perks like free breakfast, late checkout, or upgrades, and compare against OTAs like Booking.com."
💡 What it does:
AI can watch the price like a hawk, saving you the mental load of refreshing every day. Adding the direct booking check often uncovers extras that make a deal even better.
💥 What I learned:
I booked a Rome hotel for $180 less just by waiting one week. And by booking direct when the price dropped, I got free breakfast and a room upgrade…perks worth another $100+.
🛠️ Tool I used:
I paired ChatGPT with Hopper for alerts. Hopper caught the price drop, and ChatGPT compared package perks to make sure I booked the best overall value.
🌍 Prompt #3: Find Alternative Airports Nearby
🧠 Prompt to use:
"Find the cheapest international airports within 150 miles of Boston for flights to Paris in April. Include the top 5 departure options, driving or train times, estimated transfer costs, and whether the savings outweigh the transfer expense. Highlight any airports known for fewer delays or better on-time performance."
💡 What it does:
This expands your options beyond your home airport and factors in the “hidden” costs like time and transport. Sometimes the best fare is hiding just a short drive or train ride away.
💥 What I learned:
I ended up flying out of Providence instead of Boston. The flight was $140 cheaper and the Amtrak ticket cost me only $12. The smaller airport was quicker to get through, too.
🛠️ Tool I used:
I pulled baseline fares from Google Flights, then used Rome2Rio for transfer info. ChatGPT calculated the net savings after travel costs.
💳 Prompt #4: Maximize Credit Card Travel Perks
🧠 Prompt to use:
"Given these travel credit cards I have — Amex Platinum, Chase Sapphire Preferred, and Capital One Venture X — compare which one gives me the best net value for booking a $1,200 flight to Tokyo. Factor in earning rates, statement credits, lounge access, and travel insurance. If two cards are close, suggest a tie-breaker based on perks I might actually use on this trip."
💡 What it does:
This ensures you’re getting the most from the perks you already pay for. It’s like having a personal points strategist tell you exactly which card wins for each booking.
💥 What I learned:
I booked through the Amex portal, earned 5x points, and got a $200 airline fee credit…something I had never claimed before. That was like an instant upgrade without paying extra.
🛠️ Tool I used:
I pasted my card benefits and current offers into ChatGPT. It laid out the math in plain English so I could see the winner instantly.
🕵️ Prompt #5: Uncover Hidden Airline Fees
🧠 Prompt to use:
"List every possible extra fee I might pay on this low-cost airline from New York to London, based on their current terms and baggage policy. Include carry-on size limits, seat selection fees, boarding priority, and payment surcharges. Suggest the most cost-effective way to get the extras I care about without overpaying."
💡 What it does:
This prevents the dreaded “cheap fare shock” when your final price jumps by $100+ in fees. It also shows if a “full service” airline would actually cost the same or less.
💥 What I learned:
A $299 fare turned into $468 after all the baggage and seat fees. I ended up booking on a different airline that was $20 cheaper overall and came with free meals and bags.
🛠️ Tool I used:
I sent ChatGPT the airline’s fee policy page. It broke everything down and even suggested cheaper fare bundles that included the extras I wanted.
🎯 Prompt #6: Predict Price Trends for My Route
🧠 Prompt to use:
"Based on historical fare data for the past 5 years, predict whether Boston to Honolulu in July will rise or fall in the next 60 days. Give me a probability breakdown, the risk of waiting, and a recommended booking window. Include the average fare difference if booked 3 months out vs. 1 month out."
💡 What it does:
This turns guesswork into data-backed decision making. Instead of wondering “should I wait?”, you know the likely outcome.
💥 What I learned:
For Hawaii, prices were likely to jump by $200+ if I waited. I booked immediately and locked in a $280 saving.
🛠️ Tool I used:
I used Google Flights for historical trends and let ChatGPT analyze the risk vs. reward of waiting.
🛏️ Prompt #7: Find Cheaper Stays with Similar Amenities
🧠 Prompt to use:
"Find hotels in Barcelona under $200/night with amenities similar to Hotel Arts Barcelona — pool, ocean view, central location — sorted by best guest reviews. Include boutique hotels and explain why each is a good alternative."
💡 What it does:
It’s like telling AI, “I love this hotel’s vibe, but not the price.” You get the same experience without draining your budget.
💥 What I learned:
I found a boutique hotel for $160/night with the same sea views and a rooftop pool. The smaller size meant faster service and a more personal feel.
🛠️ Tool I used:
I shared Hotel Arts’ amenities with ChatGPT and asked for Booking.com listings that matched at a lower price point.
📍 Prompt #8: Bundle Activities for Discounts
🧠 Prompt to use:
"Find combination packages in Reykjavik that include Blue Lagoon entry, a Golden Circle tour, and airport transfers. Compare the total cost of bundling vs. booking each separately. Include details on what’s covered, cancellation policies, and whether booking direct with the operator offers a better deal than through Viator or GetYourGuide."
💡 What it does:
Helps you see the true savings from bundling experiences together, instead of paying full price for each. AI can also catch if third-party booking sites are tacking on hidden fees.
💥 What I learned:
I saved $75 by booking a local operator’s combo deal instead of separate tickets. They even threw in a small-group upgrade for free.
🛠️ Tool I used:
I had ChatGPT compare package prices from Viator, GetYourGuide, and the tour company’s own website. It laid out exactly where I’d save the most.
✈️ Prompt #9: Compare Flight + Hotel Packages
🧠 Prompt to use:
"For these dates in Cancun, compare the cost of booking this flight and hotel separately vs. as a package through Expedia, Costco Travel, and the airline’s vacation portal. Include whether packages come with extras like meals, transfers, or resort credits that affect overall value."
💡 What it does:
This makes sure you’re not overpaying for convenience. Sometimes a package isn’t cheaper, but other times it includes perks worth hundreds.
💥 What I learned:
A package through the airline’s site saved $210 compared to booking separately and included free airport transfers. I wouldn’t have spotted it without running the comparison.
🛠️ Tool I used:
I pasted Expedia, Costco Travel, and airline vacation package links into ChatGPT for side-by-side analysis.
📆 Prompt #10: Find Shoulder Season Sweet Spots
🧠 Prompt to use:
"For Santorini, identify the cheapest 2–3 week windows in 2025 where the weather is still warm and sunny but prices are at least 25% lower than peak summer. Include average hotel rates, flight costs, and crowd levels for each window."
💡 What it does:
Pinpoints the “goldilocks” weeks when you get great weather without the high-season prices or crushing crowds.
💥 What I learned:
Late September gave me 75°F days, calm seas, and $500+ in savings on lodging compared to July. Restaurants were quieter, too.
🛠️ Tool I used:
ChatGPT analyzed historical climate data and flight/hotel price trends from Google Flights and Booking.com.
🚖 Prompt #11: Calculate Total Trip Cost (Not Just Flights)
🧠 Prompt to use:
"Estimate the total cost of a 7-day trip to Tokyo for two, including flights, hotels, meals, transportation, and activities. Factor in my preference for mid-range hotels, public transit, and 2–3 splurge meals. Also include a 10% buffer for unexpected expenses."
💡 What it does:
Stops you from focusing only on flight prices and underestimating the total spend. This kind of planning can prevent running out of cash mid-trip.
💥 What I learned:
Flights were only half my expenses. The real savings came from swapping a few taxi rides for public transit and finding lunch spots locals love instead of tourist traps.
🛠️ Tool I used:
I gave ChatGPT my travel style and “non-negotiables,” then it pulled average costs from online data.
🛂 Prompt #12: Find Countries with Free Stopovers
🧠 Prompt to use:
"List airlines that offer free or low-cost stopover programs on routes from Boston to Bangkok. Include example itineraries, stopover length limits, and what’s covered (like hotel nights or city tours)."
💡 What it does:
Turns one trip into two for the same airfare. You can explore an extra city without adding a separate flight.
💥 What I learned:
I booked on Icelandair and got three days in Reykjavik for free on my way to Asia. It broke up the long journey and felt like a bonus trip.
🛠️ Tool I used:
I asked ChatGPT to search current stopover offers, then cross-checked with airline pages.
🛶 Prompt #13: Find Local Booking Discounts
🧠 Prompt to use:
"Check if booking these activities in Bali in person is cheaper than reserving online from the US. Include recent walk-up prices from travel forums and whether there’s a risk of tickets selling out for my dates."
💡 What it does:
Helps you decide if you should pre-book or wait until arrival.
💥 What I learned:
I saved 40% on a snorkeling trip by booking directly in Ubud after I landed. The operator even added a complimentary lunch that wasn’t advertised online.
🛠️ Tool I used:
ChatGPT scanned TripAdvisor forums, Reddit threads, and travel blogs for recent on-the-ground pricing.
📦 Prompt #14: Identify Free Perks at My Hotel
🧠 Prompt to use:
"List all complimentary perks at Hotel XYZ in Lisbon based on its website and guest reviews. Include things like breakfast, welcome drinks, shuttle service, and any unadvertised freebies mentioned by past guests."
💡 What it does:
Uncovers extras you might miss that add real value to your stay.
💥 What I learned:
I found out my hotel had free breakfast, daily wine tastings, and complimentary city walking tours…all things I would have paid for otherwise.
🛠️ Tool I used:
I combined the hotel’s official amenity list with review site mentions, then had ChatGPT summarize everything.
🛫 Prompt #15: Negotiate with Hotels or Hosts
🧠 Prompt to use:
"Write a polite, personalized message asking an Airbnb host for a 10% discount on a 2-week stay in the off-season. Mention my flexibility, excellent guest reviews, and willingness to book immediately if they can offer the rate."
💡 What it does:
Gives you a professional, persuasive template that increases your chances of a “yes.”
💥 What I learned:
I got $150 off my Lisbon Airbnb just by asking the right way. The host appreciated my polite tone and quick decision.
🛠️ Tool I used:
ChatGPT wrote a short, warm message that I sent directly through the Airbnb platform.
My Final Thoughts
These 15 prompts have made booking travel cheaper, easier, and way less stressful. Once you start using AI like this, you’ll stop wondering if you overpaid. You’ll know you didn’t.
💡 Want my full list of travel prompts and booking tools?
👉 [Grab the free Prompt Pack here]
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