KAYAK, part of Booking Holdings (NASDAQ: BKNG), is the world's leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package.
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KAYAK, part of Booking Holdings (NASDAQ: BKNG), is the world's leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package.
Launched on April 30th, 2025
Launched on February 21st, 2019
Launched on February 28th, 2018
AMA HOST WILL GO LIVE ON MAY 7TH @ 11AM EST
Hello everyone! Matthias here. As Chief Product Officer at KAYAK, I lead our AI initiatives and development of intelligent travel interfaces.
First thing I'll say is that AI in travel is deceptively complex. Many companies claim to have "solved" it, but most solutions fall short in critical ways - either they don't access real-time pricing, they hallucinate travel information, or they create frustrating user experiences.
KAYAK
Today, KAYAK is officially rolling out KAYAK.ai where real-time travel information meets conversational search. Unlike other AI platforms, KAYAK.ai delivers the most up to date, comprehensive travel pricing from 400+ providers in a chat-first format that travelers can trust.
Built combining OpenAI’s technology with KAYAK’s intelligence, the site will serve as the company’s innovation lab for analyzing how travelers engage with KAYAK tools, data and insights conversationally. As KAYAK.com’s tech savvy sibling, it will cater to AI enthusiasts and those drawn to advanced technology. What works best on KAYAK.ai will graduate to KAYAK.com.
Below are a few recommended prompts to get you started:
“Which weekend in October has the cheapest flights from Boston to London?”
“When should I fly to Chicago for a 4 day trip?”
“I’m looking for flight options from NYC to London from July 3 to July 8”
I am looking for a hotel in New York with free breakfast. Checking in July 3 and checking out July 8”
@kellermatth Would be awesome to add multi-city trip planning in one go!
KAYAK
@masump Thank you, multi-city planning is definitely something on our minds. You can already search for multi-city flights for known dates, for example just try "I want to fly from Boston to San Francisco on July 5, then continue to Singapore on July 10, and return to Boston on July 20."
@kellermatth Perfrect idea but how do you balance the flexibility of open-ended chat with the structured nature of travel data (like fare classes, room types, filters)? It feels like a tricky UX challenge 🤔
KAYAK
@hamza_afzal_butt Thank you for your feedback. It's definitely a challenge but at the same time it opens up a number of great opportunities such as prompting for very specific results or searching for a flight and a hotel in the same prompt.
@kellermatth Very cool. How did you decide on the suggested queries? It seems for a new user modality those are quite important and need to return some solid results.
Its exciting to think of the voice possibilities here.
Congratulations on the launch!
KAYAK's chat-first approach is a very good differentiator in terms of a more intuitive and personalized user exp. compared to forms (I hate those). I am curious about how you ensure the pricing data stays up to the minute accurate across so many providers?
Also, imagine if "real-time travel info" was "real time-travel info"
KAYAK
@pranay12 We pull in pricing directly from our travel providers API’s. We know price accuracy is critical for anyone booking travel and given how quickly prices change - this is always something we are investing time in at KAYAK – so kayak.ai has a strong foundation here with being built on kayak.com search technology.
Being able to chat your way through travel plans makes everything so much easier and less stressful. Big congrats on the launch!