Can ChatGPT book flights and hotels for you?

Short answer

Partly. ChatGPT can find flights and hotels and do most of the booking, but the final step is yours. The Expedia and Booking.com apps search inside the chat and then send you to their own sites to book. ChatGPT Work's cloud browser, on paid plans other than Go, can sign in to a site and fill in a booking, then asks you before it books or pays. To have ChatGPT work in a browser that's already signed in to your own airline and hotel accounts, and that your other assistants can use too, add Upsy. It takes about ten minutes.

What ChatGPT can book on its own

What changed this year:

• ChatGPT agent is gone. OpenAI retired agent mode in favour of ChatGPT Work and its cloud browser.
• Signing in works, in ChatGPT only. At a login, Work's cloud browser shows a secure form for your password and code, and stays signed in for later tasks. Those sign-ins are ChatGPT's alone; Claude, Grok and Muse don't get them.
• Payments stay with you. ChatGPT confirms with you before booking or paying. OpenAI says never to paste card details into the chat.
• Some sites refuse automated browsers, even when they work in yours. Then you take over or finish it yourself.

If ChatGPT is the only assistant you use and you're on Plus or Pro, Work's cloud browser may be all you need.

Where Upsy fits

Upsy gives your assistants your own browser in the cloud. You sign in once, in Upsy, to your airline, hotel loyalty program or rail operator, and the logins persist.

• One browser for every assistant. ChatGPT, Claude, Grok, Muse and your ChatGPT dot all use the same signed-in browser. Each works in its own tabs, labelled with its name.
• You watch and take over. Open Browser in Upsy to see the assistant work live. Click anywhere in the page to take over, for example to enter your card or solve a CAPTCHA. Upsy doesn't pay or solve CAPTCHAs for you.
• Your travel details, once. Write your home airport, seat preference and loyalty programs in Upsy's Memory. Every assistant you connect reads the same Memory, so you don't repeat yourself in each one.
• A record. Upsy's History lists every page each assistant opened and every click, under that assistant's name. It never records what was typed.

What you need

• A free Upsy account at upsy.ai.
• ChatGPT on the web, with the option to add a custom MCP server (a connector that lets ChatGPT use another app). OpenAI doesn't say which plans have it; if it isn't under Plugins, your plan or workspace doesn't allow it.
• Accounts on the sites you want to book with.

Set it up

1. Sign up at upsy.ai with "Set up Upsy".
2. Open Browser in Upsy and sign in to your airline, hotel and travel sites, as you would on your own computer. If you use 1Password, click Enable 1Password there so it can fill your logins.
3. Open Memory and write what any assistant should know when it books for you: home airport, seat and meal preferences, loyalty programs, who you usually travel with.
4. Open Assistants, click Add assistant, and under Which assistant? pick ChatGPT. Upsy shows these steps with the address to copy.
5. In ChatGPT on the web, open Plugins, click Add, then choose to create a custom MCP server. Name it Upsy, paste https://upsy.ai/connect, and set authentication to OAuth. Accept the warning, then click Create as a plugin. The custom connector guide has more detail.
6. Click Connect if ChatGPT asks. Sign in on the Upsy page that opens and choose what ChatGPT can use. Turn on the browser and Memory.
7. Upsy then shows a short "remember" message. Paste it into ChatGPT so it reaches for Upsy in new chats without you naming it.

Check that it works

Send ChatGPT: "Use Upsy's browser to open my airline account and list my upcoming trips."

ChatGPT should ask you to approve the browser action, then report what the page shows, and Upsy's Browser page shows a new tab under ChatGPT's name.

What a booking looks like

Say you ask for a flight to Lisbon on the 14th, back on the 20th.

1. ChatGPT reads your Memory: home airport, aisle seat, the airline you collect miles with.
2. It opens the airline's site in its own tab, signed in, and searches your dates.
3. It reports the fares. You pick one.
4. It fills in passengers and seats, then stops at payment, as you asked.
5. You open Browser in Upsy, take over, enter your card and confirm.

Prompts to try

• "Find nonstop flights from my home airport to Lisbon on Nov 14, back Nov 20. Compare them, and stop before payment."
• "Check my hotel loyalty account for a free night, and look for a room in Chicago Dec 3–5 that I can use it on."
• "Find a morning train from Boston to New York next Friday and fill in the booking. I'll pay."
• "Find the next DMV appointment near me and fill in the form, but don't confirm it."
• "Check me in for my flight tomorrow and tell me if I need to do anything else."

Troubleshooting

ChatGPT asks for approval at every click

ChatGPT asks before each tool that isn't marked read-only. You can remember your approval for a tool within one conversation; a new conversation asks again.

The site says you're signed out

Some sites end sessions after a while. Sign in again in Upsy's Browser page, and the assistant uses the new session.

The site shows a CAPTCHA or blocks the browser

Take over in Upsy's Browser page, solve it, and tell ChatGPT to carry on. If a site keeps refusing, book that one yourself.

ChatGPT says it isn't allowed to use the browser

You haven't given ChatGPT the browser. On Upsy's Assistants page, open ChatGPT and turn it on. It works in the same chat.

The price changed at checkout

Fares move, and Expedia warns that results in the chat can be out of date. Check the price on the payment page.

Security and privacy

• Sign in to sites yourself, in Upsy's Browser page, never in the chat. ChatGPT doesn't get your passwords; it calls Upsy's tools, and Upsy acts in your browser.
• Upsy has no approval step of its own. The confirmation before each action comes from ChatGPT.
• Browser sessions are encrypted with a key of your own, per Upsy's privacy policy, and you can delete your saved browser at any time.
• One click on the Assistants page turns ChatGPT off in Upsy, or turn off just its browser.

FAQ

Can ChatGPT book flights for me?

It can search and fill in the booking, but you finish it. The Expedia app sends you to Expedia, and both ChatGPT's cloud browser and Upsy's leave payment to you.

Can ChatGPT book hotels?

Yes, up to the payment. Booking.com and Expedia hand you off to their sites. Signed in to your hotel account, ChatGPT can also use your points or member rates.

Can ChatGPT book train tickets?

Not inside the chat. Some rail operators, such as Eurostar, have ChatGPT apps that search fares, then send you to their site. Otherwise ChatGPT fills in the booking on the rail site in a browser, and you pay.

Can ChatGPT book appointments?

Restaurant tables, yes, through OpenTable, Resy and Yelp. For a DMV or doctor's appointment, it fills in the site's form in a browser and asks before confirming.

Will ChatGPT pay for me?

Not through Upsy: you enter payment yourself. A ChatGPT dot can buy with a card saved on a merchant's site, with your approval.

Does this work with Claude too?

Yes, with the same browser and Memory: see Can Claude book flights and hotels. For other forms, see Can ChatGPT fill out forms.