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Booking flights with
Claude Cowork.
How to set Claude Cowork up to book your travel end‑to‑end: the exact project setup, the instruction template I paste in, the prompt I actually send, and the safety rules I bake in after ten years in cloud security.
i.The context
Sunday 31 May 2026, Arsenal lift their first league title in 22 years. I'm in Dubai, and I only find out on the Tuesday that I can actually make it. That leaves 72 hours to book a flight around my fairly particular preferences. (I'm a picky traveller. I've made peace with it.)
So I open Claude Cowork, type two sentences, and watch it open a browser, compare prices, go straight to Emirates, and book the flight. Eight minutes, hands off the keyboard the whole time.
Ten years in cloud security taught me one rule I won't break: never let an agent write to anything that holds my money. The setup below is built entirely around that.
It's roughly the same pattern Boris Cherny, the Anthropic engineer behind Claude Code, used to book eight flights and five hotels in parallel. Here's the whole thing: a three-step setup, the copy-paste instruction template, the two prompts I reuse, and the three safety rules.
Open Cowork and create a Project.
I called mine Flight Assistant. Call yours Travel. You can split it into Personal and Client later if you need to.
Three clicks
Open the Claude desktop app. Cowork lives there, not at claude.ai. Click Projects → New Project. Name it.
Why a Project? Because the instructions you write next live inside it. Every chat you start in Travel already knows your preferences, so you never re-explain yourself.
Flight Assistant
What would you like to work on in this project?
Paste these standing instructions.
In the project's instructions field, paste the template below and edit the highlighted parts. Claude doesn't have you memorised yet. The five minutes you spend here is what makes every trip after it a single sentence.
# Role You are my travel assistant. You operate Claude Cowork. You can open a browser, navigate sites, compare options, and complete bookings for me. # Standing preferences - Home airport: [DUBAI · DXB] - Loyalty: [EMIRATES SKYWARDS · ID XXXXXXXX] - Cabin: [ECONOMY EXTRA LEGROOM] under 6h / [BUSINESS] over 6h - Seat: [AISLE, NEAR THE FRONT] - Budget signal: Not the cheapest. The fastest direct flight that respects my loyalty, and the closest decent hotel to where I'm actually going. - Hotels: 4-star+, breakfast included, walking distance to my real destination, not the city centre by default. - Travellers: Ask if anyone else is coming and expect their passport details. Validate expiry before booking; flag if it falls within 6 months of travel. # Hard rules - NEVER book a flight with more than 1 connection unless I approve it. - NEVER book a hotel without breakfast unless I approve it. - NEVER book outside a 7-day cancellation window without confirming first. - For ANY booking over [AED 10,000]: pause, show me the option, and wait for "approved" before continuing. # Workflow 1. Confirm destination, dates, and purpose (so you pick the right area). 2. Search flights first. Show me the top 3. Wait for me to pick. 3. Ask about hotels. If yes, rank the top 3 by proximity to my address. 4. Ask about ground transport. 5. Book in order: flight → hotel → transport. 6. After each booking, paste the confirmation number and the cancellation deadline into the chat. # Output When you're done, give me a one-page itinerary in markdown: flights, hotel, transport, costs in AED, and every cancellation deadline.
Start a chat. Type the trip.
Open a new chat inside the Travel project and describe the trip in a sentence. When it's done you get a one-page itinerary, or a ping to finish any step it got stuck on.
The one I actually sent
Book me Dubai to London arriving by Saturday afternoon, May 30, for the Arsenal parade on Sunday May 31. Returning Tuesday June 2, any time after lunch. No hotel or airport transfer needed. I've arranged those.
The template: fill the brackets
Book me <origin> to <destination> arriving by <date/time> for <purpose>. Returning <return date + preference>. I want a hotel near <area>. Add the <train or transfer> from the airport.
One small trick. The first time, I told Cowork to stop at the payment page. Then I handed it a single-use virtual card: capped limit, set to auto-delete. If it ever leaked it was already worthless. Belt and braces.
For the Arsenal trip: eight minutes from hitting enter to booked, while I carried on working in Claude Code in another window.
The two prompts you'll actually use.
You know when, you know where
Book me [ORIGIN] to [DESTINATION] arriving by [DAY/TIME], returning [DAY/TIME]. Hotel near [ADDRESS or NEIGHBOURHOOD]. Purpose: [one line, so you pick the right area].
Flexible dates: let it hunt
I want to be in [DESTINATION] for [3/5/7] days sometime in [MONTH]. I can't travel [DATES]. Find the best window: the cheapest direct flight from my home airport that lands in the morning. Then book a hotel near [PLACE].
The second one is where it starts to feel like magic. It'll surface a Tuesday-to-Saturday window you didn't know was cheaper.
The safety section. Read this one.
I spent ten years in cloud security, consulting for some of the world's biggest banks. It comes down to three rules.
Rule 01 · Money
Pre-set the payment method. Don't let Cowork choose.
Save one specific card as default on the airline and hotel sites you use, ideally one with travel fraud protection and a modest limit. That's the only card it can reach. Don't leave a high-limit business card sitting there as default.
Rule 02 · Threshold
Use the approval threshold. Religiously.
Keep the line: for any booking over AED 10,000, pause and wait for "approved". Set the number to your comfort. Mine's about AED 10,000. It's the single most important guardrail.
Rule 03 · Trust
Watch the first booking.
Sit and watch the browser navigate the first time. It's genuinely fascinating. It clicks around like a person. After two or three runs you'll trust it and walk away. But let the first one earn it.
Real numbers from the Arsenal run.
What I'd test next.
Once travel is working, the same Project pattern works for plenty else. Three I'd try first:
Once you trust Cowork on a flight, you'll trust it with the rest.