How to use AI to find "hidden city" flight savings

Reading Time: 3 min

If you feel like prices for airfare are all over the place these days, you're not hallucinating. Flight prices can change from one hour (or one minute) to the next, and costs for some itineraries don't even make sense. For example, you might find a lower price for a longer itinerary, whereas a short one-way trip costs more than it really should.

One trick for finding airfare deals is using an AI prompt that focuses on something called hidden city ticketing.

Hidden city ticketing (sometimes called skiplagging) is a pricing quirk that happens when a connecting flight is cheaper than a nonstop route to the same destination. Instead of flying all the way to the ticketed final stop, you get off at the layover city and skip the last segment of the itinerary.

It sounds simple, but it comes with some important caveats. Airlines prohibit this practice in their contracts of carriage, and it doesn’t work for round-trip tickets where the return leg is still needed. Checked bags are also a major no-no, since they’re sent to the final destination on the ticket.

If you're willing to jump through a few hoops and take a few risks, however, hidden city ticketing can help you save.

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Instead of guessing which layovers might be cheaper, you can use a structured prompt to have an AI tool scan for possible hidden-city opportunities. The key is being specific about your route and travel date.

Here’s a prompt you can use:

I’m flying from [origin] to [destination] on [dates]. Search for cheaper itineraries where my actual destination is a layover city rather than the final ticketed destination.

Include:
The full flight routing
The city where I would exit the trip
The ticketed final destination
Total price comparison versus regular nonstop or standard connecting flights
Which airlines offer the hidden-city fare
Estimated savings
Information on one-way itineraries only

Make sure the comparison is for the same class of airfare only, and on the same or similar tier airline(s). Format the results in a simple table with columns for airline, route, layover city, hidden-city exit point, ticketed final destination, and estimated savings.

While AI tools may or may not search live fares for your exact dates in real time (depending on the one you're using), they will all generally reveal what to search for to find hidden city ticketing.

After typing this prompt into ChatGPT for a specific route, for example, I uncovered the following:

• Albuquerque → Minneapolis → Chicago itinerary on Delta that’s priced lower than a direct Albuquerque → Minneapolis flight

While writing this, I did a quick search on Google Flights and found a Delta basic economy flight from Albuquerque to Chicago with a layover in Minneapolis for $217. Theoretically, you could fly this itinerary and get off the plane in Minneapolis instead of continuing to Chicago.

Meanwhile, booking a direct flight from Albuquerque to Minneapolis on Delta would set you back $359 on the same date.

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Hidden city ticketing can look like an easy win on paper, but airlines have built-in rules and operational realities that can quickly turn a “deal” into a headache.

Potential risks include:

• Cancellation of remaining itinerary: If you skip a leg of your flight, the airline will typically cancel the rest of your itinerary automatically.
• Being charged for full itinerary: If an airline determines you intentionally skipped a flight, they may attempt to retroactively charge you the difference between the discounted fare and the cost of a direct ticket to your intended destination.
• Banned from airline: Airlines typically reserve the right to suspend frequent flyer accounts, revoke miles, or even restrict future bookings if they believe a traveler is abusing fare rules.
• Checked bag issues: Checked bags are always routed to the final destination listed on the ticket, not the layover city where you plan to exit. That makes hidden city itineraries effectively carry-on only.

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