Anywayr wrote this. We make one of the tools below, so we have tried to be fair and say where Expedia, Kayak and Booking.com are better.
The short answer
ChatGPT and Claude cannot see airline seats on their own. To get real fares in the chat you add a travel app or connector. Three things separate them: whether they cover flights at all, how you finish the booking, and whether they need an account.
- Browse flights with no account, then book on the company's site: Expedia, in ChatGPT and Claude.
- The widest flight search with price alerts and forecasts: Kayak, on kayak.com, where its Ask AI chat runs on ChatGPT technology.
- Hotels and rental cars rather than flights: Booking.com. Its connector pages do not describe flight search.
- Search, get an exact quote and check out in the same chat, as part of a saved trip: Anywayr.
Side by side
| Anywayr | Expedia | Kayak | Booking.com | |
|---|---|---|---|---|
| In ChatGPT | Yes, through developer mode (directory listing in review) | Yes, an app in ChatGPT | A ChatGPT plugin was announced in 2023. We could not open a current app page | Yes, an app in ChatGPT |
| In Claude | Yes, Connectors directory (Community label) | Yes, Connectors directory (Anthropic verified) | No Kayak connector found in Claude's directory | Yes, Connectors directory (Anthropic verified) |
| Flights | Yes: exact legs, up to 9 passengers, four cabins | Yes | Yes, on kayak.com | Not described on its connector pages |
| Sign-in | Anywayr account | Not required in Claude | Not described | Not required in Claude |
| Exact quote before booking | Yes, an expiring quote with the total and terms | Not described | Not described | Not applicable |
| Where you book | Anywayr checkout page. In Claude, VS Code and Codex, optionally in the chat with your saved card for fully refundable bookings within your limit | Expedia: you "click Book on Expedia" | On Kayak or the provider's site; "the booking is with the provider" | Not applicable for flights |
| Price alerts | In apps Anywayr has approved | Not described | Yes, plus a 7-day price forecast | Not described |
| Currency | US dollars | Not described | Not described | Not applicable |
"Not described" means the company's own page or listing does not say it; it does not mean the feature is missing.
Checked on 5 Nov 2026. Sources:
- Anywayr, MCP server reference, Add Anywayr to Claude, Add Anywayr to ChatGPT; Claude directory, Anywayr.
- Claude directory, Expedia; Expedia, Expedia in ChatGPT.
- Kayak, KAYAK on ChatGPT (23 Mar 2023), Ask AI (14 May 2026) and Search and discovery help.
- Booking.com, Booking.com connector and rental cars in ChatGPT (20 May 2026).
What Anywayr returns for a flight search
Anywayr's Claude listing says it covers over 380 airlines. A search needs exact legs (from, to and date for each), the passengers and a cabin: economy, premium economy, business or first. Up to 9 passengers can fly on one search, children need their real ages, and results come back up to 10 at a time, priced in US dollars.
A typical exchange:
Search flights from Chicago to Lisbon on March 12, 2027 for two adults and get the cheapest option ready for me to review.
The assistant shows the options, then asks Anywayr for an exact quote on the one you pick. The quote shows the total and the fare's terms, and it expires. From there:
- In ChatGPT, you always get a link to Anywayr's checkout page, where you enter passenger and payment details and pay.
- In Claude, VS Code and Codex, you get the same link by default. If you ticked "book with your saved card" on the Anywayr connect screen, the assistant can book a fully refundable fare in the chat, within the limit you set on your Anywayr profile, after showing you the exact total.
Anywayr's MCP reference also lists a flight deals tool that looks for low fares from one airport to anywhere, or to a region or country, across the next year, using Google Flights quotes. It is not in the tool list on the Claude directory listing, so ask the assistant whether your connection offers it. Price watches are only for apps Anywayr has approved.
Where Expedia is better
- No account in Claude. You can search flights straight away.
- Easier to add in ChatGPT. Expedia is an app you add from ChatGPT. Anywayr needs developer mode for now.
- Your Expedia account. Expedia says bookings show up in the Trips section of Expedia, which suits you if you already keep trips there.
Where Kayak is better
- Search tools built for flights. Kayak's help pages describe price alerts, a forecast of whether a fare is likely to rise or fall in the next 7 days, flexible dates within 3 days either side, Explore for when you do not know where to go, and Hacker Fares that combine one-way tickets.
- Many providers in one search. Kayak says Ask AI shows "bookable options from hundreds of travel partners", with flight, hotel and rental car results beside the chat.
- Free, with no setup. Kayak says Ask AI is free for all users.
The catch for this article: Kayak's current AI chat runs on kayak.com rather than inside your ChatGPT or Claude conversation, and Kayak's help page says it is "a travel search engine, not a ticket seller".
Where Booking.com is better
For flights, it is not the tool to reach for in an assistant: its Claude connector searches stays, and its ChatGPT app covers stays and rental cars. For the hotel half of a trip, it needs no sign-in to search. We compare it with Anywayr in Booking.com vs Anywayr.
Where Anywayr is better
- The fare you see is the fare you pay. You get an exact, expiring quote with the terms before you open a checkout page.
- You finish from the chat. A checkout link in ChatGPT; in Claude, VS Code and Codex, optionally a saved card booking for fully refundable fares within your limit.
- Flights belong to a trip. The same connector saves a trip with dates and travelers, searches hotels for it, and gives you a page your group can open. See planning a trip in Claude or in ChatGPT.
- Cancelling. If a fare would give you a full refund, the assistant can cancel it in the chat when you say yes. Anything with a fee finishes on anywayr.com.
The honest limits
Anywayr is US dollars only, needs an account, and does not offer price forecasts, Hacker Fares or rental cars through its connector. Whether developer mode shows up in ChatGPT depends on your plan and workspace.
Which should you use?
- Just looking at fares: Expedia in ChatGPT or Claude, with no account.
- Hunting the lowest fare over weeks: Kayak on kayak.com, with alerts and forecasts.
- Ready to book, or booking for several people: add Anywayr to Claude or ChatGPT.
More options: travel connectors for ChatGPT and Claude.
