Anywayr wrote this. We make one of the two tools, so we have tried to be fair and say where Kayak is better.
The short answer
People search for "Kayak in ChatGPT" because Kayak was one of the first travel companies to work with ChatGPT. Today, though, the two tools sit in different places.
- Kayak's AI chat, Ask AI, runs on kayak.com. Kayak says it combines Kayak's travel data with ChatGPT, and it searches flights, hotels and rental cars across hundreds of partners. You book on Kayak or with the provider.
- Anywayr runs inside your own ChatGPT conversation, through developer mode, and inside Claude. It searches hotels and flights, gets an exact quote and hands you its checkout page.
So: pick Kayak to hunt for the lowest fare with alerts and forecasts. Pick Anywayr to plan, quote and book from the chat, especially for a group.
Side by side
| Kayak | Anywayr connector | |
|---|---|---|
| Where the AI chat lives | Ask AI on kayak.com, which Kayak says uses ChatGPT. A ChatGPT plugin was announced in March 2023; we could not open a current Kayak app page in ChatGPT | Inside ChatGPT (developer mode; directory listing in review), Claude (Connectors directory, Community label), Claude Code, VS Code, Codex CLI |
| Claude | No Kayak connector found in Claude's directory | Yes |
| What it searches | Flights, hotels and rental cars | Hotels and vacation rentals, flights, and saved trip plans |
| Breadth | "Bookable options from hundreds of travel partners" | Anywayr's hotel and airline suppliers; its Claude listing says over 5 million hotels and vacation rentals and over 380 airlines |
| Price tools | Price alerts, a 7-day price forecast, flexible dates of 3 days either side, Explore, Hacker Fares | Exact expiring quotes. Price watches only in apps Anywayr has approved |
| Who you book with | "KAYAK is a travel search engine, not a ticket seller." You finish on Kayak or the provider's site, and "the booking is with the provider" | Anywayr's checkout page. ChatGPT is checkout-link only |
| Sign-in | Not described | Free Anywayr account |
| Currency | Not described | US dollars only |
| Group planning | Not described for Ask AI | A shared trip page with voting and cost splitting |
| Price to use | Kayak says Ask AI is free | Free to connect, plan and search. You pay for what you book |
"Not described" means Kayak's page does not say it; it does not mean the feature is missing.
Checked on 5 Nov 2026. Sources:
- Kayak, KAYAK is now integrated on ChatGPT (23 Mar 2023).
- Kayak, KAYAK.ai: our travel test lab (10 Apr 2025).
- Kayak, Ask AI (14 May 2026) and Search and discovery help.
- Anywayr, Add Anywayr to ChatGPT and MCP server reference; Claude directory, Anywayr.
What we could and could not confirm about Kayak in ChatGPT
Kayak's own newsroom has a March 2023 post announcing a ChatGPT integration, rolled out first to ChatGPT Plus subscribers. In April 2025 Kayak wrote that it had "integrated with KAYAK ChatGPT and Microsoft Copilot, among others." In October 2025 it launched AI Mode on kayak.com, which became Ask AI in 2026.
ChatGPT's app pages ask you to log in, so we could not read a current Kayak listing there, and none of Kayak's own pages we checked describe a current app inside ChatGPT. If you see one in your ChatGPT, it may work differently from what is described here.
Where Kayak is better
- Finding the cheapest fare. Kayak's help pages describe price alerts, a forecast of whether a route's price is likely to go up or down in the next 7 days, flexible date search within 3 days either side, Explore for when you are open on where to go, and Hacker Fares that combine one-way tickets. Anywayr's connector has none of these except watches, and those only in apps Anywayr has approved.
- Breadth. Kayak compares many providers at once. Anywayr shows what its own suppliers offer.
- Rental cars. Kayak's Ask AI covers cars. Anywayr's connector does not.
- Nothing to set up. Ask AI is on Kayak's homepage. Anywayr in ChatGPT needs developer mode, and whether you see that depends on your plan and workspace.
- Currency. Anywayr is US dollars only.
Where Anywayr is better
- It stays in your chat. You do not switch to another site to search. ChatGPT or Claude calls Anywayr, and the results come back in the same conversation, next to everything else you have asked.
- One company from search to booking. Kayak sends you to a provider, and the final price and terms come from that provider. With Anywayr you get an exact, expiring quote with the total and cancellation terms, then pay on Anywayr's checkout page.
- Booking in the chat, where you allow it. In Claude, VS Code and Codex you can let the assistant book fully refundable bookings with your saved card, within a limit you set. It is off by default. ChatGPT always uses the checkout link.
- A saved trip. The same connector saves a trip with its own link, builds a day-by-day plan, and keeps the hotel and flight searches tied to its dates and travelers.
- Groups. Friends join the trip page, vote on stays and plans, and see who owes whom, with Venmo and Cash App links. See planning a group trip with AI.
- Claude. Kayak has no connector in Claude's directory that we could find. Anywayr is listed there.
Who should use which
- Watching a fare for weeks, or flexible on dates: Kayak.
- Need a car as well: Kayak.
- Ready to book from ChatGPT or Claude, with the exact total first: Anywayr.
- Planning with friends: Anywayr, then use Kayak to sanity check fares if you like. Nothing stops you using both.
Add Anywayr to ChatGPT or Claude. For a walk through in ChatGPT, read planning a trip in ChatGPT with Anywayr. For more flight options, see searching flights in ChatGPT and Claude and travel connectors for ChatGPT and Claude.
