My younger self’s mindset around travel was something to be admired. I was hellbent on getting to the destination of choice — whether that meant setting multiple flight trackers, familiarizing myself with the country’s day-to-day or connecting with friends who had traveled there before. I never once considered the steps involved to safely arrive, with everything I needed, at said location.
Then I grew up, and became overwhelmed by the reality of the travel process. I had recently used AI to help me plan a road trip, but I needed something to help with international travel, too. This is how I learned about Kayak.AI, a new arm from the travel search company Kayak.
What is Kayak.AI, and how does it use AI?
Kayak was publicly launched in 2005 by co-founders Steve Hafner and Paul M. English as a travel search engine. Kayak.ai is the new, conversational AI arm that launched in early 2025. Its AI features include comparative shopping and natural language prompts.
Since it’s in beta mode, it is a space for internal experimentation — new features are distributed on Kayak.ai first before being integrated on Kayak’s site.
“We’re reimagining how people plan and book trips, making the experience faster, smarter,” Matthias Keller, Kayak’s chief product officer, says. “[With Kayak.ai] a single prompt like ‘family beach week under $2K in July’ now produces a full, personalized plan. That’s the difference between AI that just responds and AI that co-pilots the whole journey.”
Additionally, Kayak.ai doesn’t rely on cached (or sometimes outdated) information. Instead, its AI travel tool pulls live from over 400 providers so it has access to real-time pricing.
How to use Kayak.ai to create an international itinerary
While Kayak has an app, Kayak.ai is considered a web-based AI travel assistant, and these steps apply to navigating your desktop or laptop screen.
- Head to Kayak.ai and sign in or sign up. If you already have a Kayak account, this can sync with your regular Kayak trips.
- Describe your trip to the AI-powered chat assistant, using as many details as you can. I went for the whole vision: “Two-week breath taking, sight-seeing trip from Los Angeles to Tokyo in November, check-in luggage, under $1,000 and full of ease.” The Kayak.ai team shared with me that using thematic prompts that create a “vibe” help generate better results.
- Kayak.ai will show the Cheapest Time to Travel, and you can also share with it how you want to fly or stay — for example, “no red eyes,” “free breakfast,” “non-stop only.” I was asked to edit for more specific dates I wanted to travel in November before I started adding hotel rooms and other parts of my travel I had imagined. (Oh, and ask the chat assistant to bundle your options to save time.)
- You can then title your trip, share with friends (read only) and use Kayak.ai’s real-time delays feature to stay on top of your alerts and updates related to your trip, even if you haven’t booked yet.
- When you’re ready to book, the AI chat remains in your workspace for any adjustment for follow-ups.
Pro Tip: Kayak.ai said to use the cheapest weekend feature by asking: “I’m flying to Copenhagen in September, what’s the cheapest time to visit?” This will result in a price graph showing the lowest-cost weekends and how fares fluctuate across the month.
Of course, since the platform is in beta and is considered a conversational AI agent, don’t paste sensitive personal information into the chat. The company’s privacy policy is available on its site.
Who should use Kayak.ai?
This is an important question. Since it’s positioned as a beta innovation sandbox, I’d recommend this tool for tech-forward travelers. (If you’re reading this article, I would consider you one.)
I also think planners and those who love a good deal will have a great time with Kayak.ai — by comparison, I remember spending hours toggling between three different search engines to find flights. While you are trusting that Kayak.ai is pulling the best information for you, the ease of not tiring yourself out with constantly searching is a selling point.
And if you’re someone who enjoys tech and enjoys being in beta testing mode as part of Kayak.ai’s power users, this can be a really nice way to figure out your next adventure.
