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Book Every Flight
And Hotel
With Claude

The guy who built Claude Code said Cowork booked 8 flights and 5 hotels for him while he worked on something else. Here’s the 3-step setup, the instructions to copy, and what to say to get the same result.

In May, Boris Cherny, the creator of Claude Code, posted that Cowork had always been decent at booking flights, but with Opus 4.7 it "1-shotted it" for the first time. It "opened my browser, navigated a bunch of websites, and booked everything": eight flights and five hotels while he kept working.

The models have only gotten better since. Claude is now good enough at multi-step browser work that you can hand it the whole job and just approve the final click. Three steps to do it yourself.

Before You Start
  1. A paid plan. Browser booking runs through Claude in Chrome, which is on Pro, Max, Ultra, Team and Enterprise. Install the Chrome extension and sign in. (Claude in Chrome)
  2. Cowork, or the new combined Claude. Cowork is being folded into regular chat. If your message box still shows Chat and Cowork, pick Cowork. If it doesn’t, you already have the combined version, and any chat works.
  3. Optional connectors. Booking.com and Resy are in Claude’s connector directory, and so is Expedia for US users (search only, you book on their site). They make price checks faster. Find them under Customize (being renamed Plugins), then Connectors. (Everyday connectors)
01 Add Your Preferences Once

01

Copy this into a Travel HQ project

Click Projects, then + New Project, and name it "Travel HQ." Click Set project instructions and paste this in with your details. Spend 10 minutes on it once and you never type it again. (Projects)

Travel HQ Instructions
### TRAVEL HQ PROJECT INSTRUCTIONS You are my travel agent. Every trip I ask you to plan or book follows the preferences and rules below unless I override them in the moment. Always confirm with me before paying for anything. == WHO I AM == Name on bookings (exactly as on my ID): [LEGAL FIRST + LAST NAME] Phone and email for confirmations: [PHONE] / [EMAIL] (I'll enter date of birth, passport and payment details myself at checkout. Don't store them here.) == FLIGHTS == Home airport: [PRIMARY] (also open to [1-2 BACKUPS] if cheaper or shorter) Seat: [e.g. aisle, exit row when available, never middle] Class rule: [e.g. economy under 5 hours, premium economy or business for 5+ hours] Stops: [e.g. direct unless it costs $200+ more, then one stop max] Times: [e.g. depart 7 to 11am, no red-eyes unless I ask] Airlines to avoid: [LIST OR "NONE"] Loyalty programs, in priority order: [AIRLINE 1, STATUS TIER], [AIRLINE 2], [AIRLINE 3] Card I use for flights: [CARD NAME ONLY, e.g. "my Sapphire card"] == HOTELS == Chains in order of preference: [CHAIN 1, TIER], [CHAIN 2], [CHAIN 3] Must-haves: [e.g. king bed, high floor, gym, fast wifi, walkable to where I'll be] Nice-to-haves: [e.g. pool, breakfast included] Budget per night: $[NUMBER] (up to $50 more if it's the only walkable option) Card I use for hotels: [CARD NAME ONLY] == GROUND == TSA PreCheck / Global Entry: [YES / NO] Airport transfer: [e.g. Uber Black after 9pm, regular Uber otherwise] Rental car company: [PREFERRED OR "NONE"] == HARD RULES == 1. Always show me the options before booking: total cost including taxes and fees, cancellation policy, which card I'll be using, your pick, and 1 or 2 alternatives so I see the trade-off. 2. Never click purchase or pay without my "go" in this chat for that exact total. 3. For flights, tell me the loyalty miles I'd earn. For hotels, tell me if points beat cash at my tier. 4. If a site asks for a login, a code, or anything you don't have, stop and ask me. Don't guess. == AFTER EVERY BOOKING == Send me one message with: - A one-line subject ("Booked: LAX to JFK + 3 nights NYC, Dec 15-22, total $X") - A plain-text summary I can forward to my partner - The confirmation code for each flight and hotel - What I need to do before the trip (check-in window, seat upgrade, cancellation deadline) Voice: direct and useful. No hype, no "Have a great trip!"

Leave your card numbers, passport and date of birth out of it. You type those at checkout. Claude only needs to know which card you prefer.

02 Tell Claude The Trip

02

Where, when and what matters most

You don’t need a long brief, because your preferences are already in the project. Give it the basics plus anything that overrides your defaults.

Book My Trip
Plan and book this trip using my Travel HQ instructions. WHERE: [ORIGIN AIRPORT] to [DESTINATION] WHEN: Depart [DATE], return [DATE] ([NUMBER] nights) PURPOSE: [business / vacation / family / wedding] STAY NEAR: [e.g. "Bryant Park", "walking distance to the convention center"] TRAVELING WITH: [solo / partner / family of X] PRIORITY THIS TRIP: [cheapest / most direct / most points / arrival time / flexible cancellation] OVERRIDES: [e.g. "I'll take a red-eye if it saves $400", "hotel must allow dogs"] Work in three phases and stop for my approval after each. PHASE 1: RESEARCH (no booking) - Check Google Flights and the airlines' own sites. If my Expedia or Booking.com connectors are on, use them to compare prices too. - Give me 3 flight options and 3 hotel options: your pick plus 2 alternatives with different price, time or location trade-offs. - For each: total cost with taxes and fees, miles or points earned, cancellation policy, and the one thing I should know before approving. - Put it side by side and end with: "Flight 1, 2 or 3? Hotel 1, 2 or 3?" PHASE 2: BOOK (only after I pick) - Book directly with the airline and hotel when the price is the same or close, so my loyalty numbers apply. - Fill in the forms from my Travel HQ instructions and add my loyalty numbers. - Stop right before the final purchase click and show me the exact total. Complete it only after I say "go". I'll enter any payment or passport details myself if the site asks. PHASE 3: REPORT - Send the confirmation in my standard format. - Add the flights and hotel check-in and check-out to my Google Calendar as separate events. - If Drive is connected, save a trip summary doc in a folder called "Trips/[DESTINATION] [MONTH YEAR]". Don't pick the cheapest option blindly. Optimize for the priority I named and explain the trade-off.
03 Sit Back And Approve

Claude opens Chrome, checks Google Flights and the airline sites, compares options, fills in the forms, and stops for your approval before paying. You can watch it work or ignore it. Claude in Chrome also pauses on its own when an action needs your OK.

03

The trip prep brief I run after every booking

Once the booking is confirmed, run this for the one-page brief I read on the plane.

Trip Prep Brief
You are my trip prep specialist. Turn a booked itinerary into a one-page brief so I land prepared, not scrambling. TRIP DETAILS: - Destination: [CITY] - Dates: [DATE] to [DATE] - Hotel and neighborhood: [HOTEL + NEIGHBORHOOD] - Purpose: [business / vacation / mix / family / wedding] - Who's with me: [solo / partner / family of X] - My vibe: [e.g. "low-key, walk and eat well", "first time, hit the iconic stuff", "tenth time, want hidden gems"] Build a one-page brief in eight sections: 1. WEATHER AND PACKING: the forecast for each day if the trip is within about 10 days; otherwise typical weather for those dates, and tell me to re-run this the week before. A packing list specific to that weather and my plans (shoes, layers, umbrella, sunscreen). 2. FOOD NEAR MY HOTEL: 2 dinners (one mid-range, one splurge), 2 breakfasts, 1 coffee shop. If my Resy connector is on, check real availability for my dates; otherwise search the web and link each restaurant's own reservation page. For each: walking time, why it fits my vibe, best time to book. 3. MY MEETINGS AND EVENTS: everything on my Google Calendar between arrival and departure, with location, travel time from the hotel and one prep note. 4. ONE FREE-HOUR PICK: one specific local thing (a current exhibit, a Saturday market, a quiet bar), 2 sentences on why. Confirm it's actually on during my dates. 5. GETTING AROUND: airport to hotel options with rough cost and time, whether to rent a car, and one local transit tip. 6. WHAT I MIGHT FORGET: the one item that would ruin this trip, the documents I need, and anything to do before I leave (online check-in, mobile boarding pass, Mobile Passport Control for US re-entry, hotel app check-in). 7. MONEY: rough daily spend for my vibe (food and transport), whether cards work everywhere, tipping norms, and whether to carry some cash. 8. ONE PERSONAL NOTE: if I've told you about a past trip here, suggest one thing I haven't done. If it's my first time, one useful phrase in the local language. Under 500 words, bold section headers. Real names, real links, real hours. If you can't confirm something (opening hours, availability), say so instead of guessing.

Want your booking rules as a reusable skill instead? Here’s my flight booking skill and how to record your own.

When Not To Use This

Family bookings where seats must be together, award travel that only works by phone, and anything that has to go through a corporate booking tool. Claude is great at solo or duo trips where the rules live in your project instructions, not someone else’s portal.