Anywayr wrote this. We make a group trip planner, so we have tried to be fair and say where the others are better.
The short answer
Plan the first draft wherever you already chat. If it is just you and you want ideas fast, ChatGPT is a good place to start, and its Expedia app adds hotel and flight results inside the chat. If you are planning with other people, or you want the plan to still be there when the chat is closed, a dedicated planner fits better. Claude is also a general assistant, and it connects to outside tools, including Anywayr.
- ChatGPT on its own: best for brainstorming, quick questions and general knowledge, with no sign-up to a travel site.
- ChatGPT with the Expedia and Booking.com apps: best when you want Expedia hotel or flight results, or Booking.com rental car options, without leaving the chat, then finish booking on the partner's site.
- Anywayr: best for a group that needs one shared plan, votes and a cost split.
- Claude with connectors: best when you want a general assistant that can also reach tools you choose, including Anywayr.
What changed in ChatGPT
ChatGPT now has apps, and two of the first were travel brands.
OpenAI announced apps in ChatGPT on 6 October 2025 and named Booking.com and Expedia among its pilot partners. OpenAI describes the way they work: you can call an app by name, or ChatGPT can suggest one at the right moment, and the first time you use an app ChatGPT asks you to connect it. OpenAI's help centre now calls these "connected apps" and says availability depends on your plan, region, workspace, role, model and interface.
Expedia. Expedia's own page says its app gives "dynamic flight and lodging results powered by Expedia, including pricing, availability, and rich visuals" inside ChatGPT. Its launch notice says the app is available to logged-in ChatGPT users outside of the EU on Free, Go, Plus and Pro plans. Booking is not finished in the chat: Expedia says "click Book on Expedia" to be taken to Expedia to finish, and your booking then shows in the Trips section of Expedia.
Booking.com. OpenAI's launch post lists Booking.com as a pilot partner. Booking.com's own announcement of 20 May 2026 covers rental cars: people describe what they want and get options to browse, and are "seamlessly redirected to Booking.com to complete their reservation." We did not find a Booking.com page of its own that lists everything the app does, so we describe only that.
So ChatGPT plus these apps can search and show options. On both pages we read, the booking itself happens on the partner's site.
Connectors and developer mode
The Model Context Protocol (MCP) is an open standard that lets an AI assistant call outside tools. OpenAI's launch post says its Apps SDK for ChatGPT apps builds on MCP.
ChatGPT also has developer mode, which lets people add their own MCP apps. OpenAI's developer mode help page says developer mode and full MCP support are available to ChatGPT Business and Enterprise/Edu customers on ChatGPT web, and that admins or owners turn it on. OpenAI's pricing page lists "Developer mode (beta)" as Yes for Plus and Pro and No for Free and Go. The two OpenAI pages name different plans, so check your own account before counting on it. Not every ChatGPT user can add a connector like Anywayr's.
Claude works on the same standard. Claude's help centre says custom connectors using remote MCP are available on the Free, Pro, Max, Team and Enterprise plans, and that Free users are limited to one custom connector.
Where Anywayr fits in AI assistants
Anywayr has a connector, so an assistant can plan a trip, search hotels and flights, get a quote, and hand back a link to Anywayr's own checkout. You sign in to your Anywayr account when you connect.
According to Anywayr's connectors page, it works today in Claude, in ChatGPT in developer mode only, and in Claude Code, VS Code and Codex CLI. Grok, Google Gemini, Meta Muse, Mistral Le Chat, Perplexity and Microsoft Copilot Studio are listed as coming soon. Anywayr is not a listed ChatGPT app, and developer mode is limited to the plans OpenAI names above. Planning and searching through the connector are free. The full list is at anywayr.com/connectors.
Side by side
| ChatGPT on its own | ChatGPT with Expedia and Booking.com apps | Anywayr (group planner) | Claude with connectors | |
|---|---|---|---|---|
| Itinerary building | Yes, in chat | Yes, in chat, with app results mixed in | Day-by-day group itinerary from destination, dates, travelers, budget and interests | Yes, in chat |
| Live prices | Not stated on its pricing page | Expedia: "pricing, availability" for flights and lodging. Booking.com: rental car options to browse | Hotel and flight search. Rentals and activities show options and link out | Not stated on its pricing page. Connectors you add can supply them, such as Anywayr |
| Group planning (shared plan, voting, cost splitting) | Shared projects are listed on its pricing page for every plan. Voting and cost splitting are not stated there | Not stated on the apps' pages we checked | Invite friends by link, vote on stays and rental cars, cost splitting with Venmo and Cash App settle-up links | Project sharing not included on Free, Pro or Max. Group features come from the connected tool, such as Anywayr |
| Booking | Not stated on its pricing page | Link to partner (Book on Expedia, Booking.com reservation) | In-app checkout for hotels and flights. Rentals and activities: link to partner | Depends on the connector. Anywayr's connector hands back Anywayr's checkout link |
| Keeps the plan after the chat ends | Chat history, plus memory (limited on Free) | Same as ChatGPT. Expedia bookings appear in Expedia Trips | Trips can be listed and reopened after you sign in, including from a connected assistant | Memory across conversations and Projects. Anywayr's connector can list and reopen your Anywayr trips |
| Price | Free $0, Go $8, Plus $20, Pro from $100 a month | Same ChatGPT plans. Expedia lists its app as available on Free, Go, Plus and Pro | Planning is free. Optional Early Supporter plan, $15 a month | Free $0, Pro $17 a month annual or $20 monthly, Max from $100 |
Checked on 30 Sep 2026. Sources:
- OpenAI, Introducing apps in ChatGPT (6 Oct 2025).
- OpenAI help, Connected apps in ChatGPT.
- OpenAI help, Developer mode and MCP apps in ChatGPT.
- ChatGPT, Pricing.
- Expedia, Expedia in ChatGPT and launch notice.
- Booking.com, Booking.com is making car rentals easier with app in ChatGPT (20 May 2026).
- Claude help, Get started with custom connectors using remote MCP.
- Claude, Pricing.
- Anywayr's own pages: /connectors, /plan, /faq, /about, /terms.
"Not stated" means the source page does not say; it does not mean the feature is missing. Plans and prices change, so check each site before you decide.
What a chat does well, and where a trip gets harder
For one traveller, a chat is hard to beat for the early stage. You can ask for ideas, change your mind, ask "what about somewhere warmer in March?" and get an answer at once.
The harder parts come later.
Several people. A chat is one person's conversation. A group needs a place where everyone sees the same options, says yes or no, and knows what they owe. Anywayr is built around that: an invitation link, votes on stays and rental cars, and cost tracking with Venmo and Cash App settle-up links. The money moves in those apps, not in Anywayr.
Keeping the plan. ChatGPT and Claude both keep history, and both have memory features, though ChatGPT's memory is limited on the Free plan. A trip saved in a planner is something you can reopen, instead of a thread to scroll.
Booking. With the Expedia and Booking.com apps, you search in the chat and book on the partner's site. Anywayr offers its own checkout for hotels and flights, and links to partners for rentals and activities. We are not claiming that one route is better. The best route is the one that shows the price you want.
Where ChatGPT is better
- Speed to a first idea. You type a question and get an answer. You do not fill in a form first.
- General knowledge. ChatGPT is a general assistant, so questions, writing and research can sit in the same conversation as the trip.
- No new account for a planner. If you already use ChatGPT, you can start now. Its Free plan costs $0.
- Access to Expedia and Booking.com inside the chat. If you want Expedia flight and hotel results, or Booking.com rental car options, without opening another site, the apps do that, on the plans and in the regions they list.
- One place for everything else. The same assistant is not limited to travel, so you do not need a separate tool for each job.
If you are planning alone, or just gathering ideas, these are clear advantages.
Which should you pick?
- Just you, early ideas: ChatGPT or Claude. Start there.
- You want priced options in the chat: ChatGPT with the Expedia app, then book on Expedia.
- A group of friends or family: a planner with invitations, votes and cost tracking. Start a trip on Anywayr.
- You like to work in an assistant but want a saved group plan: connect Anywayr to Claude, or, if your plan has developer mode, to ChatGPT. See anywayr.com/connectors.
Many people will use more than one. For a comparison of trip planners beyond chat assistants, see the best AI trip planners in 2026.
