Paiback: The AI Travel Assistant That Gets You Money Back on Flights — Automatically

When is the best time to book a flight? Months in advance or a few weeks before the flight? It varies by flight, capacity, carrier, and other variables that only the airlines know. But now it doesn’t matter and something you need not be concerned about.

With a new service from a company called Paiback, you can book well in advance and have them act as your agent to insure you’ll get the lowest fare between when you book and when you fly. The company uses AI automation to get your money back when the airfare drops — doing all the work on your behalf.

Its model is simple and easy to use: upload your airline ticket, as long as it’s booked directly through the airline — not through third parties like Amex, Expedia, or Chase – and Paiback’s AI-powered bots monitor your fare. If the price drops, their AI bot contacts the airline on your behalf, and gets you a credit or refund for the difference. 

You pay a 20% commission on the amount Paiback saves you. They check the fare every 3 hours, 24 hours a day, so it’s more than likely they’ll capture a number of price drops between the time you book and when you fly. If the fare doesn’t drop, you pay nothing, but can take some satisfaction that you snagged the lowest fare.

Unlike generic travel alerts from Google or Expedia, or doing it yourself, Paiback acts as your own personal travel assistant. The bot calls or chats with the airline, waits on hold for as long as it takes, and requests the lower fare. If it’s a refundable ticket, it may secure a cash refund. If it’s nonrefundable, Paiback gets you a travel credit.

“We could all technically do this ourselves,” Phil Parrotta of Paiback told me, “but it takes time, effort, and knowledge most travelers don’t have. Our goal is to automate what savvy travelers used to do by hand.”

Paiback currently works with tickets from Delta, United, American, and Alaska, for all classes of service except basic economy. Since COVID, most major airlines have eliminated change fees for all but the basic economy tickets, making post-booking fare drops eligible for credits. Of course, the airlines don’t automatically notify you — and you can only get the credit if you call the airline and request it. Paiback simply automates the process.

Parrotta provided some findings from their service:

  • About 60% of tickets drop in price after booking.
  • The average savings Paiback users see is around $250 per person.
  • For international flights in premium cabins, refunds or credits have reached as high as $5,000.
  • On many flights, prices drop multiple times before departure.
  • The company is currently tracking over $2 million worth of airline tickets

You’re only billed once you’ve received the adjustment. If you decide not to take your flight, you still pay the 20% of any savings found, but you receive the savings for use on another flight.

“We’re pro-traveler and pro-airline,” says Parrotta. “When travelers feel protected, they’re more confident booking earlier. That leads to better planning for the airlines — and more loyalty from the customer.”

Are there any downsides? You’re trusting a new company with your flight information and assuming their process will not disrupt your reservation. The site provides no details on whether their service ever encounters technical issues or has any risks, although the technology they are using is not unlike a service Google once offered for using bots to make restaurant reservations.

I’ve not yet tried Paiback. Reviews on Trustpilot are positive, although most reviewers have only reviewed one or two other businesses prior and they are all about the same 5 months old. I’d like to see a lot more recent first hand reviews on their site.

The process Paiback has created, using AI is intended to give us a tool to counter the AI airlines use to maximize their revenue, and is a good use of AI’s capabilities. Its effectiveness comes down to how well it’s implemented and devoid of any unintended consequences, as well as the willingness of an airline’s customer service agent to speak with a bot. Of course, eventually our bots will be speaking with their bots.

In the meantime, Paiback says it offers human backup to its AI. While bots handle much of the work, there’s a human team ready to step in when edge cases arise.

You can sign up at paiback.app