(Bloomberg) -- Whether you’re tired of second-guessing your ability to find the best summer airfares or coming up blank on your next vacation idea, Kayak is betting on the power of generative AI to zap your travel planning woes.   

On Tuesday, March 5, the metasearch site owned by Booking Holdings Inc. released a duo of Chat GPT-powered trip-planning tools it says will streamline your shopping decisions, both by helping you figure out what you’re looking for and then making it easier to compare pricing. The first, Ask Kayak, builds on the company’s popular Explore tool by using a free-form, text-based chatbot to help you home in on the right vacation spot.

With Explore, you toggle around a map that highlights airfare costs as you zoom in and out of various destinations and regions. Ask Kayak goes a step further: You can query the chat bot for airfares to places that fit not only your budget but your preferred time zone, flight length or type of activities. It offers a shortcut to finding, say, the rare beach vacation that doesn’t require astronomical airfares and lies within a five-hour radius of your home airport.

The second tool, Kayak PriceCheck, is more of a comparison shopper for airfare: Once you’ve found a flight you like on any website, screenshot the route and upload it into the Kayak app, which will scour more than 100 partner sites for the best price possible on that specific ticket. In theory, you could do this by using the filtering tools on a Kayak airfare search, but PriceCheck makes it faster and more efficient to cross-check prices. In theory, it limits search results to fares that match (or closely compare to) your already established choice.

Kayak is hardly alone in leveraging generative artificial intelligence to simplify travel planning. Online travel companies including Hopper, Expedia, Booking.com, Priceline and GetYourGuide have integrated AI for such features as price prediction or chat-based assistance. Even filtering a hotel search for properties with accessible rooms makes use of AI. Still, these tools speak to the ways that AI can fundamentally change the way we plan and book travel. For one thing, they all attempt to move away from familiar interfaces that require us to start any travel purchase by entering dates and destination.

“We have a long history of using machine learning and AI technologies. They just are usually behind the scenes,” says Matthias Keller, chief scientist and senior vice president of technology at Kayak. The new features, Keller adds, use AI in a way that’s “more visible to the user.”

Shoppers should see the new tools in the Kayak app starting this week; Ask Kayak will also be accessible on kayak.com. We’ve already put them to the test. 

Kayak PriceCheck

Keller tells Bloomberg that PriceCheck is able to find cheaper fares than such competitors as Google because it searches more places. Rather than selling air travel on its website, Kayak’s business model is to find good deals and send customers elsewhere to book them, taking a cut from each referral. This is both a benefit and a liability. Kayak’s partnerships with third-party sites may help find better pricing, but they expose customers to some risk: When you book through a third-party rather than directly through an airline, you’re probably out of luck should you ever need to reach customer support.If that’s a risk you’re willing to take, PriceCheck may serve you well. Not only will it search hundreds of providers for the best price on your preferred route, it will pull up the next-best alternatives based on potential savings. In our tests, it took some 30 seconds to learn that the specific $1,330 roundtrip flight we’d found from Washington D.C., to Rome in mid-May would cost $60 less on Gotogate than on Tap Portugal, which was Google’s pick.   

Were we willing to select an alternate route, we could save $464, the tool said. But the itinerary it suggested wasn’t comparable at all. Rather than offering a direct flight like the one we’d originally selected, the cheaper option required an overnight layover in Copenhagen on the way home. Factor in the cost of added accommodations, food and transport, and our bottom line would have been damaged.

Other tests showed similar results. For a round-trip flight from Los Angeles to London’s Heathrow Airport on Memorial Day weekend, Kayak PriceCheck told us we had already found the best priced flights, at $1,107 nonstop on Virgin Atlantic. It made two suggestions: Set up a price alert in case of a fare drop, or opt for a Norse Atlantic flight to London’s Gatwick Airport to shave $47. 

if you use the tool enough, you’ll find that Kayak’s providers are extensive but not exhaustive. The best flight we found on Google Flights for a September trip to Cairo was $812 round-trip on Qatar Airways; Kayak PriceCheck could not find that itinerary but listed an alternative that would cost $62 less by flying Saudia—bookable via low-cost sites oojo, Crystal Travel or mytrip. (Always be sure to do due diligence on third-party sites before employing them; some have poor reputations.)

Keller says results will depend on how soon you plan to travel: The closer you are to your desired dates, the less likely you’ll be able to land big savings. 

Ask Kayak

Find Ask Kayak either by heading straight to its dedicated website or via the menu that spans the left side of Kayak’s homepage. It will offer the option to set your home airport above a search bar that asks, “What are you looking for in your next trip?” 

Dismayed at the thought of spending more than $1,300 on an economy roundtrip flight to Rome, we asked Kayak to find European alternatives with better pricing. Using our predetermined travel dates—which we submitted anew—Kayak suggested Barcelona (airfares from $426), Budapest (from $623), Athens ($704), Prague ($601) and Lisbon ($704), among others. Responses showed not just airfare but starting hotel prices on a clear interface that made it easy to budget for the big picture.

In a second query, we asked Kayak to play travel agent and start a vacation plan from scratch. We told it we wanted an international beach destination less than three hours from New York City in the East Coast time zone, with flights costing less than $400 per person. Kayak suggested Montego Bay, Jamaica ($344), Punta Cana, Dominican Republic ($294; note the one-hour time change), Cancun, Mexico ($347), San Juan, Puerto Rico ($332), and Nassau, Bahamas ($366). The same query for a ski destination in March yielded Montreal ($333) and Burlington, Vermont ($391).

Seeing hundreds of destination options whittled down to five offers a sense of clarity and relief. It’s a solid improvement over scrolling the Explore map, which is more entertaining than productive. And the Kayak option is more informative than simply inquiring with ChatGPT directly; that engine recommended only one destination (Bermuda) for the same query and provided no specific prices or clear booking offers. 

Still, there’s a caveat: You can’t talk to Ask Kayak as you would with Chat GPT. The text box limits each query to the length of a sentence, thereby requiring brevity and specificity. And it doesn’t let you refine your query with follow-up questions. If you wish to pursue it further, you must start afresh.

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