How to use the AI on booking sites
Most large booking sites now have an AI assistant that searches their own listings from a plain-language request, and you then book through the site as usual. Priceline's Penny and MakeMyTrip's Myra let you pay inside the chat, and Trip.com's TripGenie does so for eSIMs and attraction tickets. KAYAK's Ask AI and Skyscanner's AI search compare many providers, and you usually book with the airline or travel company. Expedia, Booking.com, Tripadvisor and Iberia also have apps inside ChatGPT, where you search in the chat and finish the booking on the company's site or a partner's.
Where to start, by situation
KAYAK Ask AI
Conversational search inside KAYAK
Compare prices across many sites: you chat while flight, hotel and car hire results from hundreds of providers update beside the conversation; you usually book on the provider's site.
Priceline Penny
AI travel assistant inside Priceline
Weigh a whole trip with one company: it compares hotels, flights and car hire with live prices, recommends a top pick and lets you book without leaving the chat.
- You book in the same app
Skyscanner Search with AI
AI search inside Skyscanner
Not sure where to go yet: describe the kind of trip and timing, and it suggests destinations compared on fare, weather, flight time and 'vibe'; in beta in English-speaking markets.
- In beta
Trip.com TripGenie
AI travel assistant inside the Trip.com app
Planning and help abroad in one app: it builds itineraries, translates menus and speech, and lets you buy eSIMs and attraction tickets inside the chat.
- You book in the same app
Booking.com AI Trip Support
AI customer-service agent inside Booking.com
Change a Booking.com stay you already have: its AI agent answers questions around the clock and can change reservations, passing complex cases to a person; in ten markets.
What matters when choosing
- Whose listings it searches: a booking site's assistant shows that site's own listings and prices; Penny, for example, books through Priceline. KAYAK and Skyscanner are comparison sites, so their AI covers many providers.
- Where you pay: Priceline, MakeMyTrip and, for eSIMs and attraction tickets, Trip.com take payment inside the chat. KAYAK (except some bookings completed on KAYAK's own pages), Skyscanner and most apps inside ChatGPT send you to another site to finish; GetYourGuide says you can book its tours without leaving the assistant.
- Who the seller is: when you book through a comparison site, you book with the airline, hotel or travel partner, and KAYAK says the airline, hotel or agency that fulfils the booking handles changes and cancellations, even when you complete it on KAYAK's site.
- Where it works: many features started in one market. Airbnb's AI search is starting in the US, Booking.com's AI Trip Planner was in its mobile app in five countries at Booking.com's last market update (October 2024), Tripadvisor's ChatGPT app is US-only and Expedia's is not available in the EU.
- In the site's app or in ChatGPT: the same company may offer both. Booking.com has AI features in its app and an app inside ChatGPT, and Tripadvisor has an AI trip builder in its app and a hotel-deal app in ChatGPT.
AI on Expedia, Booking.com and other travel sites compared
| Tool | What it helps you do | What using it involves | Limits to know |
|---|---|---|---|
| Priceline Penny | Compare hotels, flights and car hire across destinations and book in the chat. | Describe a complicated trip; Penny checks live prices, lays out trade-offs and names a top pick. | You book through Priceline. Penny's Take, a closer read on one hotel, is in beta. Source for Priceline Penny |
| KAYAK Ask AI | Search flights, hotels and car hire across hundreds of providers by chatting. | Ask from the KAYAK homepage or the iPhone app; results update next to the chat as you refine. | Mostly sends you to the provider to book; some bookings complete on KAYAK. Either way, the provider handles changes. Source for KAYAK Ask AI |
| Skyscanner Search with AI | Get destination ideas with live fares from a description of the trip you want. | Type a request such as cheap flights to Japan in December; results compare fare, weather, flight time and 'vibe'. | In beta. English-speaking markets; results are for guidance only. You book with the airline or travel partner. Source for Skyscanner Search with AI |
| Booking.com AI Trip Planner | Get destination ideas, itineraries and matching Booking.com properties with prices. | Chat in the Booking.com app; Smart Filter turns your description into filters, and Property Q&A answers questions about a listing. | Mobile app only at Booking.com's last update (October 2024), in the US, UK, Australia, New Zealand and Singapore; Booking.com says its AI is moving into an embedded companion. Source for Booking.com AI Trip Planner |
| Airbnb AI search and support | Search homes, experiences and services in your own words or by voice. | Describe what you want; results include AI-written descriptions, and wishlists compare homes side by side. | Rolling out from 30 September 2026, starting in the US. Source for Airbnb AI search and support |
| Trip.com TripGenie | Plan, get help on the ground and buy eSIMs or attraction tickets in the Trip.com app. | Chat, speak or use the camera; Live Guide and Menu Assistant help with speech and menus. | Lives inside the Trip.com app. In-chat checkout covers eSIMs and attraction tickets so far. Source for Trip.com TripGenie |
| MakeMyTrip Myra | Book flights, hotels or buses on MakeMyTrip by typing or speaking. | Type or speak in English or Hindi, per MakeMyTrip's App Store listing, and pay inside the chat. Press coverage of Myra 2.0 describes six more Indian languages and passport scanning. | Myra 2.0 rolled out in phases from May 2026; ticket and voucher upload was announced as coming soon. Source for MakeMyTrip Myra |
| Booking.com AI Trip Support | Get answers about an existing Booking.com reservation and make changes at any hour. | Ask the AI agent, or call AI Voice Support with your booking details; complex issues go to a person. | Existing bookings only; it does not plan or book. Ten markets, including the US, UK and Australia. Source for Booking.com AI Trip Support |
| Expedia app in ChatGPT | Shortlist Expedia hotels and flights with live prices inside ChatGPT. | Ask ChatGPT in plain language, then choose 'Book on Expedia' to finish on Expedia. | Not available in the EU. Needs a ChatGPT login; works on Free, Go, Plus and Pro. Source for Expedia app in ChatGPT |
Three places to find a booking site's AI
Booking sites use AI in three places. Most add an assistant to their own app or site that searches their listings, such as Booking.com's in-app AI, Airbnb's AI search, Priceline's Penny and Trip.com's TripGenie. The comparison sites KAYAK and Skyscanner use AI to turn a plain-language request into a search across many providers.
The third place is inside ChatGPT. Expedia, Booking.com, Tripadvisor and Iberia have apps you call in a ChatGPT conversation to see live options, and in each case you finish on the company's site or, for Tripadvisor, a partner's. Tripadvisor's ChatGPT app compares hotel deals from more than 400 booking sites and hotel partners, but only for US users. Hotel groups and airlines have followed: IHG, Hilton, Hyatt, Accor, Wyndham, Radisson, Virgin Atlantic and Virgin Australia have ChatGPT apps that send you to their own sites to book, and Marriott, Hilton and IHG are testing AI search on their own sites and apps. Airlines' own assistants are listed too: Qatar Airways' Sama helps plan and book in its app, Lufthansa Group's chat assistant rebooks cancelled or postponed flights, and Air France's My Trip Assistant answers baggage questions.
Paying inside the chat
A few site assistants now take payment in the conversation. Priceline's Penny lets you book without leaving the chat, and MakeMyTrip's Myra lets you pay inside the chat; press coverage of Myra 2.0 describes passport scanning to fill in traveller details. Trip.com's TripGenie lets you buy eSIMs and attraction tickets the same way; Trip.com says it started with low-risk purchases.
Despegar's SOFIA, used in Latin America on the web and in WhatsApp, recorded its first fully in-chat sale in Brazil in September 2026: a stay paid by Pix. That feature is still in testing. Otherwise SOFIA helps you explore trips and answers questions about existing bookings, passing complex cases to human advisers.
Help after you book
AI is also handling customer service. Booking.com's AI Trip Support, announced in October 2025, answers questions around the clock and can change reservations in ten markets, handing complex questions to a person, while AI Voice Support lets you manage a trip by phone on English and German lines. Airbnb offers AI chat support in more than 50 languages and is adding voice support by phone.
If you booked through a comparison site, the seller handles changes, not the site. KAYAK says the airline, hotel, rental company or agency that fulfils a booking deals with changes and cancellations, including bookings completed on KAYAK's site.
Check the label and the market
Many of these features began as betas in a single market. Skyscanner's AI search is a beta in English-speaking markets and says its results are for guidance only, Tripadvisor's AI itinerary generator launched in 2023 as a US-only beta, and Airbnb's AI search is starting in the US.
Expedia shows how quickly things move. Romie, an AI assistant it announced in May 2024 as an experimental alpha, has no official confirmation that it is still available. Expedia's May 2026 announcement still describes Trip Matching, which turns a travel Reel you share with Expedia on Instagram into an itinerary, and Expedia Group bought the AI trip planner Layla in July 2026.
Guides for this task
- Google's AI travel tools: Gemini trip planning and AI Mode Plan a trip with Gemini and Google's other travel AI: AI Mode, Flight Deals, Maps, Lens and Translate. What books, what links out and what needs a paid plan.
AI on Expedia, Booking.com and other travel sites: common questions
Does Expedia have an AI assistant?
Expedia has an app inside ChatGPT, which shows hotels and flights with live prices and sends you to Expedia to book, and Trip Matching, which turns a travel Reel shared with Expedia on Instagram into an itinerary. Expedia Group also bought the AI trip planner Layla in July 2026. Romie, its experimental assistant from 2024, has no confirmed current availability.
Does Booking.com have an AI trip planner?
Booking.com launched an AI Trip Planner in its mobile app in 2023, and at its last market update (October 2024) it was live in the US, UK, Australia, New Zealand and Singapore. In October 2025 Booking.com said its AI features were moving from a standalone planner to an AI companion across the app, so it may now appear under a different name. Booking.com also has an app inside ChatGPT for stays and car hire, which sends you to Booking.com to book, and AI Trip Support for changing an existing reservation.
What is KAYAK Ask AI?
It is KAYAK's chat search, reachable globally from the KAYAK homepage since April 2026. You ask in plain language, and flight, hotel and car hire results from hundreds of providers update beside the chat. You usually finish booking on the provider's site, though some bookings can be completed on KAYAK. It is also in KAYAK's iPhone app.
Does Airbnb have AI search?
Yes, from 30 September 2026, starting in the US. You can search homes, experiences and services in your own words or by voice. Results include AI-written descriptions of each home's key features, and wishlists can compare homes side by side with AI summaries.
Do booking site AI assistants compare prices with other sites?
Most do not. Priceline's Penny books through Priceline, and Booking.com's AI Trip Planner showed properties with Booking.com prices. KAYAK's Ask AI and Skyscanner's AI search cover many providers, and Tripadvisor's ChatGPT app compares hotel deals from more than 400 booking sites and hotel partners for US users.
