How to Use AI to Find Cheap Flights to Europe (for Under $300)
Most people drop $800+ on flights to Europe because they don’t know this exists.
I’ve flown to Spain, France, and Germany for under $300 roundtrip using one thing: AI travel prompts.
This post breaks down exactly how I do it…plus the Gemini and ChatGPT prompts I use to hack airfare like a travel pro.
👇 Let’s make your next trip ridiculously cheap.
My #1 Tool For Finding Flight Deals to Europe
Looking to save big on airfare? After 8 years and 72 countries visited as a digital nomad, here’s my go-to resource I HIGHLY recommend: Going.com (formerly called Scott’s Cheap Flights).
It’s super simple to get started. Just sign up for free, set your home airport, and choose the destinations you’d love to visit. From there, you’ll get deal notifications straight to your inbox…everything from cheap fares to mistake fares to points-and-miles opportunities.
I always recommend starting with the free version since it’s a must-have for anyone who travels. But if you’re serious about finding the best international deals (especially to Europe), Premium is where you’ll see the biggest savings. You can try it free, and if you like it, use my code JON25 to save 25% on your membership.
Why You're Overpaying for Flights (and How AI Fixes It)
After years of managing a travel website, I’ve noticed some interesting patterns on how people like to travel. Here’s what the average traveler does:
Searches once on Google Flights
Filters by nonstop + lowest price
Books whatever’s “decent”
It feels smart, but it’s surface-level.
What they don’t realize is that flight prices are algorithmically fluid. They fluctuate based on:
Your location and browsing history
Time and day you search
Departure city flexibility
Seasonal trends and mistake fares
The average traveler is up against dynamic pricing. AI levels the playing field.
With tools like Gemini and ChatGPT, you can:
Find “arbitrage cities” with hidden discounts
Track price patterns over time
Uncover mistake fares faster than the blogs
Generate booking strategies that avoid peak pricing
AI isn’t just saving time. It’s saving hundreds of dollars per trip. Here are my tops tips to save on flights to Europe in 2025-2026.
Step 1: Use Gemini or ChatGPT to Map “Flight Zone Arbitrage”
Not every flight to Europe is priced the same…even if it’s the same distance.
This is where “flight zone arbitrage” comes in.
Some European cities consistently have cheaper entry points from the U.S. because of taxes, demand, or airline hubs.
Use this Gemini prompt:
“What are the cheapest European cities to fly into from the U.S. in [month/year]? Prioritize deals under $400 and flights with 1 stop max. Please search the internet to find the best available rates”
Gemini taps live search data and flight APIs. Within seconds, it’ll spit out options like:
NYC → Lisbon = $320
Miami → Milan = $289
Boston → Dublin = $270
Book the cheapest destination first. Then use budget carriers like Ryanair or trains to get to your final stop.
One trip, I wanted Paris but booked Madrid. A $28 Ryanair flight got me across the border. I also frequently fly into airports like Reykjavik, Lisbon, and Madeira, which tend to have the cheapest transatlantic flights.
Step 2: Use AI to Compare Alternate Airports and Total Costs
Here’s the reality: the airport you fly out of matters as much as your destination.
If you live near NYC, it means you technically have three departure options: JFK, Newark, and LaGuardia. But if I stretch a bit further, Philly and Boston are also in play.
If you’re not on the East Coast, chances are your flight to Europe will route through another U.S. city first. The mistake most travelers make? Letting the airline pick that connection for them. AI flips this. You can ask Gemini or ChatGPT to find the cheapest U.S. gateway airports to Europe and then build your trip around those.
Here’s the exact prompt to drop into Gemini or ChatGPT:
Alternate Airports & Cost-Tradeoff Prompt
“Compare fares from [Your City/Region] to Europe by first flying into major U.S. hubs (JFK, Newark, Boston, Chicago, Miami, Atlanta, Dallas, LAX, SFO). Show average total costs, typical layover lengths, and which hubs consistently offer the lowest fares to Europe. Rank them by total price + convenience.”
Why this matters:
A roundtrip from Denver → Paris direct might cost $750.
But Denver → JFK → Paris could cost $480 all-in.
Sometimes it’s even cheaper to book two separate tickets: one domestic hop to a major hub, then a Europe ticket from there.
Rather than doing this research manually, AI helps by:
Identifying which U.S. hubs have the cheapest Europe routes at the time you’re traveling.
Factoring in layover time so you’re not stuck with an overnight unless it’s worth it.
Showing whether two separate bookings actually save money after baggage fees.
This is the Midwest and West Coast traveler’s secret weapon: don’t let Delta or United decide your hub. Use AI to pick the cheapest one yourself.
Step 3: Plug Results Into Flight Trackers (But Use AI to Read Them)
Once you’ve found 3–5 good routes, it’s time to analyze trends.
Use these tools:
Google Flights: Set alerts for each route
Hopper: Get booking guidance based on trend predictions
Skyscanner: Great for flexible searches across regions
Here’s where AI sharpens the edge.
Prompt for ChatGPT:
“Compare price history and future trend predictions for these routes: [paste 3 routes]. Suggest the best time to book based on past data.”
ChatGPT can read patterns that most people miss.
It’ll tell you:
“This route dropped 22% last year in early October”
“Prices rise 30 days out. Book 45–60 days in advance”
Instead of guessing, you’re booking with data-backed timing.
Step 4: Use AI to Watch for Mistake Fares
Mistake fares are real. And they’re gold.
A few times a year, airlines screw up pricing…offering Europe flights for $150–$300 roundtrip. But they don’t last.
To catch them, use this Gemini prompt:
“Track current mistake fares from the U.S. to Europe. Show only roundtrip options under $350 with departures in the next 3 months.”
Pair it with Going.com (formerly Scott’s Cheap Flights). The paid version is worth it.
Then use this follow-up prompt:
“Summarize the top 5 flight deals from my Going.com alerts this week. Highlight Europe flights, price, and departure city.”
Let AI do the scanning so you don’t have to refresh 10 times a day.
Step 5: Let AI Handle the Booking Strategy
Found a solid route? Before you book, get your strategy locked.
Prompt for ChatGPT:
“Act like a travel hacker. I want to fly to [destination] in [month]. I can depart from [city] and fly on weekdays. Suggest a 3-step plan to find the cheapest price and exact day/time to book.”
It’ll guide you through:
Best day of the week to fly
Alternate airport options
Booking delay or timing recommendations
One time, ChatGPT told me to wait 5 days for a likely drop—and it hit. I saved $80.
My Personal Win: Europe for $274 Roundtrip
I booked Boston → Madrid → Boston for $274.
The breakdown:
Gemini showed TAP Air Portugal flights dipping under $300
I cross-checked with Skyscanner and found the price trend supported it
ChatGPT gave me the best booking window based on historical drops
The kicker? I used a 9-hour layover in Lisbon to have a full Portuguese lunch by the water.
That’s how you turn $274 into an international flex.
Again- while Gemini is my go-to to search the best live deals, I highly recommend Going.com, as it tends to have even better quality flight data than other AI tools. Highly recommend signing up for the free version, and premium if you’re looking to fly abroad at least once per year.
