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Thoughts on Kayak's Ai so far?

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TL;DR

  • Kayak.ai is testing a separate AI chat interface to gather prompt data. By creating a .ai domain with chat format, they can validate demand and conversion before changing their main site, while capturing valuable "ChatGPT-like behavior" in their analytics to understand user search patterns.
  • Shared chats create indexable UGC content (doorway pages 2.0) - Users can share trip-planning conversations that are aggregated into topics and indexed via a sitemap, essentially following the Pinterest/Reddit Answers playbook, where quality-reviewed UGC creates programmatic SEO at scale.
  • Success depends on quality controls and actual usage. They need validation mechanisms (using kayak.com data) to prevent spam before indexing shares, embeddings to cluster similar intents to canonical versions, and consistent user adoption. Without real usage, creating helpful content, the entire strategy fails.
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:34 PM
Would like to get everyone's thoughts on kayak.ai - Would you consider creating an alternate .ai version of your website that's that familiar chat format?
:exploding_head: 2 :cool: 1
Kyle Faber
Kyle Faber
Oct 17, 2025, 7:37 PM
Oh wow. Not a terrible idea to prove out the demand and conversion from it before overhauling and destroying your main site. Maybe it flops (deprecate it), or is incremental (run it in parallel) or it totally blows things out of the water (replace the main).
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:37 PM
their robots.txt and sitemap are also worth contemplating over
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:38 PM
Haha I wouldn't be surprised someone in 10 Canal St is looking at this but... we're talking about you!

TLDR; It appears they want "share" pages that are created (UGC) to get indexed and served to bots... !!!
Kyle Faber
Kyle Faber
Oct 17, 2025, 7:40 PM
I was on mobile when I first looked - I see what you mean!
Kyle Faber
Kyle Faber
Oct 17, 2025, 7:41 PM
Sadly no LLMs.txt though :whitefrowningface:
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:41 PM
If they're successful in getting people to use their version... they'd get a lot of "ChatGPT-like behavior" in their app analytics
:100: 2
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:42 PM
IMO that's the 3D chess move there.
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:43 PM
Share-gating is probably a combination of oauth + you could also have a more elaborate system prompt to deter spam
Kyle Faber
Kyle Faber
Oct 17, 2025, 7:44 PM
Wheels are spinning with this
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:44 PM
 
Victor M Pan
Victor M Pan
Oct 17, 2025, 7:46 PM
Haven't figured out the criteria for sitemap inclusion yet, but :joy:
Kyle Faber
Kyle Faber
Oct 17, 2025, 8:06 PM
Looks like if the chats are shared, they’re aggregated into topics and are then available as a share route. My main very basic assumption for criteria would be:

• is it shared
• Are there N number of prompt answers available for any topic
• Is there demand for said topic (they’d have that data from kayak.com)
Victor M Pan
Victor M Pan
Oct 17, 2025, 8:06 PM
We're so back to doorway pages :upsidedownface:
???? 2
Kyle Faber
Kyle Faber
Oct 17, 2025, 8:07 PM
It’s wild out there
Victor M Pan
Victor M Pan
Oct 17, 2025, 8:51 PM
The fact that it shares by language parameters bewilders me though :joy:
James Gibbons
James Gibbons
Oct 17, 2025, 10:27 PM
Back to the pinterest playbook...
Eric Hoover
Eric Hoover
Oct 17, 2025, 10:50 PM
Honestly idk if/how/why users would use this over GPT etc but I do love the idea as a test. And yea the ability to get all that prompt data from the tool :drooling_face:
Andrew Shotland
Andrew Shotland
Oct 18, 2025, 12:26 PM
https://kayak.ai/share/sfo58yDTFR_K7bhMGC-HEXA

This is basically the Reddit Answers playbook.
Dorron
Dorron
Oct 18, 2025, 4:33 PM
I'm all for this. Planning trips and itineraries can be complex and nuanced. I used Comet to book a full trip with an itinerary and car rental and saved $257. But let's see how well it works and the adoption rate...it's good prototyping
Krinal Mehta
Krinal Mehta
Oct 19, 2025, 1:39 AM
upside is big to test
in larger orgs, at times the bureaucracy demands such moves too
???? 1
Victor M Pan
Victor M Pan
Oct 20, 2025, 2:21 PM
With a few days to think about this:

1. Kyle's right about using kayak.com data to validate - or even kayak.ai data to validate - whether a "share" is worth indexing. Some sort of "review of quality" is needed before spammers are creating "backlinks"
a. Right now their use of parameters and indexing different countries concerns me on their XML sitemap.
b. Their XML sitemap hasn't really budged since their launch, which is a good thing.
i. That being said, I haven't been messing with browser user-agents to test it (they could very well be doing this to throw off some competitors, but IYKYK)
c. We'll know this is a serious play when kayak.ai is promoted.
d. Depending on how tight they'd want to define their clusters via embeddings, you could see a lot of shares actually all redirect to a "canonical" share that's both most popular but similar in intent.
2. Doing tests like this (Throw your website as an AI chat wrapper) on a separate domain will become a new norm if LLM's to unlock data for providers of content and experiences.
3. If the app is helpful and people are sharing really helpful trip plans... then the content is actually not crap or considered doorway pages. How judicious you are with various signals to shared trip plans on indexing is what makes or breaks this UGC programmatic SEO play.
a. Spammers will need prompt engineering skills to get the right kind of response from an LLM which benefits their blackhat plays - which may also serve as a deterrent - but every hack that gets through can be collected as an edge case to train against.
b. Travel planning isn't a DAU kind of activity, let alone WAU. To make habits stick you need usage. Without usage, everything falls apart.
???? 2 ❤️ 1