Today, KAYAK, the world’s leading travel search engine, is dropping a new suite of AI products to help make travel planning decisions faster, easier and more intuitive. These innovations are the result of extensive training of ChatGPT’s AI model on KAYAK’s proprietary database of billions of consumer travel queries.
At the forefront of today’s release is KAYAK PriceCheck, a new patent-pending price comparison tool. Anyone with KAYAK’s app can upload a screenshot of a flight itinerary from any site, and KAYAK will quickly check hundreds of sites to verify they’re getting a great price.
Also launching today is Ask KAYAK – the company’s latest AI-driven innovation designed to improve and personalize the search experience. Ask KAYAK lets travelers use simple text entries to search and refine their results.
Wondering where to go with your family for spring break that’s less than 3 hours from NYC and will cost less than $300 per person? Just Ask KAYAK and you’ll get family-friendly destinations a short-distance away that fit your budget.
Travelers will also see a chat box in the results page where they can input their specific hotel, car or flight requirements. For example, they can enter “United, nonstop, morning departure, <$500” and quickly see their results. Ask KAYAK starts rolling out today and will soon be available to all users in the US, UK and Canada with more markets to follow.
But wait, there’s more. KAYAK is also introducing the following new ways to make travel planning easier:
- Check the scores. Our Provider Quality Scores gives travelers greater confidence when booking a flight by rating providers against a set of quality factors (like price accuracy, customer service, fee transparency and customer satisfaction). Scores are for Online Travel Agencies (OTAs) only.
- Compare ticket options to get what you want. View all of your options even more easily, like what is and what is not included in your flight ticket, when deciding between a basic economy, economy, premium economy or business class ticket for your US domestic flight.
- KAYAK Trips – now with live updates. With a new simplified itinerary view, KAYAK Trips keeps all your travel plans in one place – no matter where you booked. Now, not only can you build your itinerary through automatic inbox syncing, but you can also get real-time travel updates on your home/lock screens (on iOS).
- Passwords are so 2023. Passkeys are a more secure and user-friendly way to sign in to KAYAK. In fact, since implementing passkeys and ditching passwords, KAYAK reduced the average time it takes users to sign-up and sign-in by 50%.
There’s a lot of great stuff happening at KAYAK. Learn more about the features announced today HERE.

KAYAK brings Conversational AI powered by ChatGPT to the world of travel
Posted in Commentary with tags KAYAK on October 15, 2025 by itnerdKAYAK, the world’s leading travel search engine, today launched AI Mode, a natural-language search experience that combines KAYAK’s data with ChatGPT to deliver smarter, contextual results, right from the home page. KAYAK is the first major travel site to let users plan complete trips by typing questions directly into a search box.
How to Use AI Mode
Travel Demand Heats Up for the Holidays
The debut of KAYAK AI Mode comes at the perfect moment for holiday travel planning, as KAYAK data shows that mid-October through early November is the prime window for scoring the best holiday travel deals.
Prompt your Way to Holiday Savings with KAYAK
To help the AI-curious, KAYAK suggests these festive, holiday-themed prompts to reveal instantly actionable trip ideas – whether it’s a snow-globe-worthy village or a New Year’s Eve bash. Try one in AI Mode or come up with your own to see where it takes you:
For tips on writing the best travel prompts, visit KAYAK’s blog.
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