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September 2025

New Features

Light mode: KAYAK.ai just got brighter. We gave it a lighter design. Same planning power, just with more daylight.
Visualized thinking: You’ll see what we see. As KAYAK.ai processes your query, we show you a behind-the-scenes look so you’re never left guessing.

 

Fixes + Improvements

Interactive filters: Now you can toggle filters in your results view. No need to retype your prompt. Just adjust on the fly.
Collapse results: Want less clutter? You can now collapse expanded results and get back to a simpler chat view.
Smarter error messages: When something goes wrong, we tell you why. Clear info, no mystery mode.

August 2025

New Features

Activities: Get recommendations on the best things to do to fully experience the destination of your choice!
Onboarding guide – Added a new suggested prompt on the front page that introduces all the best ways to use and make the most out of KAYAK.ai!

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Cheapest Time to Travel – Cars: Looking to rent a car for a roadtrip? Quickly hone in on the cheapest time to rent the perfect vehicle for your adventure.

 

Fixes + Improvements

Login Optional: Removed the requirement for users to log in or create an account before planning their dream vacation
More Pins on Map: Previously we had restricted the map view for stays searches to show a max of 3 pins for the various hotels suggested for booking. Now we will show up to 9 hotels on the map via pins.
Squashed some minor bugs

July 2025

New Features

Package search (hotel + flight): Bundle up. You can now search for package deals that combine hotel + flight offers from our partners – so you save money and avoid toggling between 14 tabs.
Front door redesign: The KAYAK.ai homepage just got a glow-up. Now it helps you kick off your planning with broader travel inspo – not just specific trip tiles. Great for when you want to go somewhere, just not sure where yet.
Conceptual hotel filters: Looking for a hotel with a view of the Eiffel Tower? Or one that’s extra walkable, romantic or moody in the right way? We now support conceptual filters – even the oddly specific ones.

 

Fixes + Improvements

Trips Sync: Trips created in KAYAK.ai now show up in your main KAYAK Trips tab. One account, all your plans, no duplicate effort.
Car search bugs, squashed: We fixed a few weird edge cases that were messing with filters like Car Type. Car results should now behave as expected.
Smarter feedback collection: You can now tell us why something worked well when submitting positive feedback. Data is nice. Context is better.
Chat sharing controls: More control over who sees what. Show your friends the getaway plan and your parents the carefully curated “we’re visiting you” itinerary. Same trip, different audience.

June 2025

New Features

Sharable chat: Did all that heavy lifting? Now you can share the chat – with none of the chaos. Create a private, read-only link to your KAYAK.ai thread and let friends or family see what you’ve got planned
Flight details page: You asked for more info, so we’re giving it to you. KAYAK,ai now includes a dedicated flight details page that lets you drill into the fine print–face conditions, baggage rules, layovers, all if it. No more guesswork, especially for complex routes or deal-hunting travelers. More transparency = smarter bookings.
Package search (coming soon): Flight + hotel + not losing your mind = coming to KAYAK.ai. Stay tuned.

 

Fixes + Improvements

Better trip navigation: We cleaned up the Saved/Planning tab so it’s easier to jump between all the trips you’ve been mentally booking since Tuesday.
Clearer “no results” messages: When filters get too picky and return nada, we now explain why. So you can adjust and keep searching—instead of wondering if the internet broke.
Trip management – now in sticky nav: Renaming or deleting a trip? Those controls now follow you as you scroll. Because important actions shouldn’t be hiding at the top of the chat like they’re shy.
Heads-up for external links: Click a link that takes you off KAYAK.ai? We’ll give you a polite heads-up first. Not a trap—just transparency.
Bug fixes + smarter testing: Squashed some small bugs and added automated QA checks to catch the next batch before they bug you.

May 28, 2025

New Features

  • Car search: Looking to rent wheels for your next trip? KAYAK.ai now helps travelers search for rental cars based on specific dates and destinations. Fewer tabs, faster trips.
  • Multi-theme destination searches: Got range? Now you can search for places that check multiple boxes – like a “romantic, foodie-focused getaway” or “outdoorsy, budget-friendly escape.” Perfect for indecisive planners and multi-hyphenate vacations.
  • New feedback modal: We gave our feedback modal a glow-up. Now it’s easier to tell us what’s working – and what’s not – so we can make KAYAK.ai even smarter. (Yes, we read them. All of them.)

 

Fixes + Improvements

  • Cheapest time to travel gets smarter: When we don’t have enough data to show the cheapest time to book, we’ll now explain why – so you’re not left guessing.
  • Source links for AI chat responses: When KAYAK.ai answers questions that don’t involve searching (aka the “chatty” ones), we now include links to our sources. Because transparency > mystery.

May 14, 2025

New Features

  • Flight status: Want to know if your flight’s on time, delayed or just generally being dramatic? Ask KAYAK.ai. You can search by flight number, airline, airport or route – and skip the gate-side anxiety.
  • Nonstop routes: Layovers are for lunatics. See every nonstop route from any airport and get inspired for your next destination… or at least your next daydream.
  • Cheapest time to travel, now for Stays: KAYAK.ai now shows you when hotel prices are actually decent. Just pick a destination and we’ll surface the dates where your dollar goes the furthest.
  • Text summaries: Too busy to scroll? We get it. Now, before we show you the full results, KAYAK.ai gives you a quick-hit summary of what’s in store. It’s like speed dating for travel deals.

 

Fixes + Improvements

  • We squashed some post-launch bugs. RIP to weird glitches 👋
  • Cheapest time to travel widgets (for flights and stays) now come with shiny new CTA buttons. Because knowing when to go is great – but booking it? That’s where the magic happens.