Book Your Flights With Claude (Free Setup Guide)

How to set up Claude to book your flights for you, the same way the engineer who built Claude Code books his. Boris Cherny recently posted that he books all of his travel with a Claude feature called Cowork, and that with the new Opus, for the first time ever, it booked an entire batch of flights in one shot. This is the exact setup. It takes about ten minutes once, and then you never scroll a booking site again.

What You'll Learn

• The exact master prompt (copy, paste, fill in your details)
• The 3-step Cowork + Chrome setup, with nothing technical
• The safety layer that means it never spends your money on its own

The whole trick: you are not booking a trip. You are teaching Claude to be your travel agent one time. The setup is the product. After that, every trip is one sentence.

What You Need

Three things, all of which you already have access to inside Claude. No code, no automations, no new apps.

• Claude, with Cowork (the mode where Claude can actually do things, not just chat)
• The Google Chrome connector (this is what lets Claude drive your real browser)
• Your travel details: passport, home airport, loyalty numbers, and the cards you pay with

Step 1: Make The Project

Open Claude, go to Cowork, and choose Projects, then New Project. Name it Travel Agent. A project is just a saved workspace that remembers everything, so you only ever set this up once.

Why a project, not a chat: a normal chat forgets you the moment you close it. A project keeps your passport, your points, and your preferences on file forever.

Step 2: Give It Hands

Go to Connectors, search for Chrome, and add the Google Chrome connector. This is the step that turns Claude from something that gives you advice into something that actually books. Once it is connected, Claude can open your browser and use the airline, hotel, and card accounts you are already logged into.

• It uses your existing logins, so your miles and saved cards are right there
• It books on the real sites (United, Delta, Expedia, hotels), not some middle layer
• You watch it happen in your own browser, so nothing is hidden

Step 3: The Master Prompt

Open the project Instructions, click the plus, and paste in the prompt below. Fill in the bracketed parts with your own details. This is the brain of your travel agent. The last block is the part most people skip and the part that matters most: it tells Claude to stop and ask before it ever pays.

You are my personal travel agent. When I give you a trip, book it end to end: search, compare, pick, fill in my details, apply my points and credits, and take it to the final review screen. ALWAYS stop and ask me to approve before you submit any payment. Never spend money without a yes from me.

TRAVELER
- Full legal name (as on passport): [NAME]
- Date of birth: [DOB]
- Passport no. / expiry / country: [...]
- Known Traveler / NEXUS / TSA PreCheck: [...]
- Home airport: [e.g. YLW] - also check [nearest big hub] if much cheaper
- Send confirmations to: [email] / [phone]

PREFERENCES
- Nonstop when possible, max one layover ~2 hours, no red-eyes unless I say so
- Aisle seat near the front, never a middle, never basic economy / no-seat fares
- Cabin: economy under 6 hours, premium economy over 6 hours
- Airlines: prefer [alliance/airline], avoid [budget carriers]
- Hotels: 4-star min, walkable area, free cancellation, under [$X]/night

LOYALTY + PAYMENT
- Frequent flyer #: [...] - only use miles when each is worth > ~1.4 cents
- Flights on [card]; hotels on the card with the best travel multiplier
- Always check if a travel credit covers part of it first

HOW TO REPORT
- Show me the 2-3 best options with one line on why, then book the one I pick
- Flag anything non-refundable or basic-economy before booking
- Stop at the payment screen every time and wait for my approval

Then Just Ask

Once the master prompt is saved, booking a trip is one sentence. Here is the exact format. Say where, when, and any constraint, then tell it to stop at the payment screen.

Book my trip to Costa Rica, out June 21, back June 29, one carry-on. Find the best flight into San Jose (SJO) and a hotel in a walkable area, then take it all the way to the payment screen and show me before you submit.

Claude opens your browser, compares flights, picks your seat, fills in your details, applies your miles and credits, and lays the whole trip out. Then it stops and waits for you to approve the payment. You can sit there and watch it, or go do something else and come back to a finished trip.

The Safety Layer (Read This)

The number one fear people have is an AI spending their money without asking. The master prompt already solves this, but here is how to keep it airtight.

• The instruction "stop and ask me to approve before you submit any payment" means it never buys on its own. It builds the whole cart, then waits
• Always do your first booking with it sitting next to you so you see how it asks for approval. After one trip you will trust it
• Keep the 1.4-cents miles rule in. It stops Claude from burning your points on a flight where the cash price was the better deal
• If it ever picks something you do not like, just tell it what to change. It re-runs the search, it does not start over

Pro Moves

Once the basic setup works, these are the upgrades that make it feel like a real concierge. Say this and it will:

• "I have 3 trips coming up, book all of them": batch the whole calendar and hand you one summary with every confirmation
• "Use my miles on the longest flight": spend points where they are worth the most and pay cash on the cheap legs
• "Build me a trip outline I can save": generate a clean one-page itinerary artifact of the whole trip
• "Watch this fare and rebook if it drops": track the price and tell you when it is worth changing

Get a trip outline: ask Claude to build you a one-page trip outline at the end. You get a clean itinerary you can screenshot, send to whoever you travel with, or save offline.

Where To Go From Here

Booking flights is the easy win. The same setup (a Claude project plus the Chrome connector) is how you build an agent for almost anything you do on a computer over and over: ordering groceries, renewing subscriptions, filling out the same forms, pulling reports. The travel agent is just the one that pays for itself the fastest.

Go Deeper

Prefer a printable version? Download the PDF: https://drive.google.com/file/d/17U2oWSi5Lpo2IDYZzbDk2CA1S_xlLzoL/view?usp=drivesdk

Want the whole system installed live, with Cooper on the call? Build Your Own AI, the two week sprint runs the first two weeks of August.

Or get a new working tool every Monday inside The AI Operator community on Whop.