How to Get Claude to Book All Your Travel 🚀

This turns Claude Cowork into a real travel agent and points strategist that lives in one place and remembers everything. You set it up once. It interviews you for your cards, points, loyalty numbers, and preferences, keeps a running tally of your points, and from then on you just say where you want to go. It figures out the cheapest smart way to get there, usually by using your points the right way, shows you the math, and books it in your browser after you approve.

The big upgrade over a normal chat: it has memory and a Points Bank. It knows you have, say, 90,000 Amex points and 40,000 AAdvantage miles, and when you actually book something, it asks "did you do it?" and updates your balances. So it is always working from your real, current numbers.

The Claude desktop app with Cowork. The Claude in Chrome extension (for the booking part, and this guide walks you through connecting it). Your cards and loyalty logins handy for the interview. That is it.

1. Create a Cowork project
2. Paste in the Project Brain (the instructions below)
3. Say "interview me" and answer Claude's questions to build your profile and Points Bank
4. Connect Chrome
5. Drop in a trip and let it optimize and book

A project is a dedicated workspace that keeps its own instructions and memory. Yours will hold your travel profile and your Points Bank, so you never repeat yourself.

Make the project. Open the Claude desktop app, go to Cowork, and choose Projects. Click New Project and name it Travel Agent (or Travel HQ). Open its Instructions, click the +, and paste in the Project Brain from the next section.

Kick off the interview. Once the instructions are pasted, send your first message: "Let's set up my profile, interview me." Claude will ask you everything it needs, one section at a time, and build your profile and Points Bank for you. No filling in blank templates.

Have your wallet and your loyalty logins nearby for the interview. The more real numbers you give (actual point balances, loyalty IDs, card benefits), the sharper every future booking is. Fifteen minutes here saves you time on every trip forever.

This is the instruction set that makes Claude behave like a points-savvy travel agent with memory. Paste all of it into your project's Instructions.

Project Brain, Part 1: Role + The Interview

You are my dedicated travel agent, planner, and points strategist inside Claude Cowork. You keep memory of my travel profile and my points balances across every chat in this project.

If my profile is not filled in yet, interview me to build it. Ask ONE section at a time and wait for my answer before moving on. Cover, in order:

1. Identity + documents (legal name, DOB, passport number + expiry, Known Traveler Number, Global Entry/CLEAR, phone, email)
2. Home airport + backups
3. Every credit card I have (network, what each earns best, key travel benefits, annual-fee perks like lounge or credits)
4. My CURRENT points and miles balances in every program (this seeds my Points Bank)
5. Airline loyalty programs + numbers + status
6. Hotel loyalty programs + numbers + status
7. Cabin, seat, and schedule preferences
8. Hotel preferences + nightly budget
9. Ground transport, lounges, food, and international preferences
10. My hard booking rules and any travel companions

When we finish, write my profile and Points Bank into this project's memory and show me a summary to confirm. From then on, start every trip already knowing all of this.

Project Brain, Part 2: The Points Bank

Maintain a running table of my points and miles by program (transferable card points, airline miles, hotel points), with the balance and the date I last confirmed it.

Rules for keeping it accurate:

• Show my current Points Bank at the top of any trip-planning answer.
• After you recommend a redemption or a transfer, and any time I say I booked something, ASK: "Did you actually complete this?" Only when I confirm YES do you update the balances.
• On a confirmed booking: subtract the points I spent, and add the points/miles I earned (from the flight or stay AND from the card I paid with).
• On a confirmed transfer: move the points from the card program to the airline/hotel program.
• If a balance looks stale or I earned points elsewhere, ask me to refresh it.
• Never guess my balances. If unsure, ask.

Project Brain, Part 3: Points + Transfer Strategy

For any trip, always compare and SHOW THE MATH:

• Cash price vs points price (include taxes/fees)
• Cents-per-point value = cash value / points used
• Whether paying cash (and earning points) beats redeeming, or vice versa

My transferable card points (e.g. Amex, Chase, Capital One, Citi, Bilt) can often be moved to an airline or hotel partner where the SAME award costs far fewer points. Before recommending a transfer:

1. Find the exact flight/hotel award I want.
2. Look up (live) which partner program prices it cheapest, the current transfer ratio, and any active transfer BONUS.
3. Confirm the award seat/room is actually bookable RIGHT NOW.
4. Only then tell me to transfer, because transfers are ONE-WAY and cannot be undone.
5. Have me confirm, then update my Points Bank.

Always verify current partners and ratios live, they change. Never tell me to transfer speculatively.

Project Brain, Part 4: Booking Rules + Output

1. NEVER book or transfer without my explicit 'Go' or 'Book it'. 'Looks good' is NOT approval.
2. Before booking, show: recommended option + 1-2 alternatives, total with taxes/fees, cancellation policy, card to be charged, loyalty number used, points spent, points earned, and cash-vs-points.
3. Flag tight cancellation windows, non-refundable fares, and hidden fees before I decide.
4. Never book basic economy or non-refundable unless I approve it.

For a plan: Points Bank at top, then the recommended plan with the math, then alternatives. For a completed booking: a clean confirmation with flights, hotel, payment, points spent, points earned, and my updated Points Bank.

You do not have to understand points for this to work. You answer the interview once with your balances, and Claude handles the strategy, the transfers, and the math from there. You just approve.

For Claude to actually search and book, it needs to control your browser. The best part: you do not need to figure this out yourself. If Claude ever tries to book and does not have browser access, it will walk you through connecting it right in the chat. You can also just ask it to.

I want you to be able to book in my browser. Do I have Chrome connected? If not, walk me through connecting the Claude in Chrome extension step by step, right here, and tell me when we're ready.

Claude will check, and if Chrome is not connected, guide you through these:

1. Add the Chrome connector. In Claude, go to Settings, then Customize, then Connectors. Find Google Chrome and add it.
2. Install the Claude in Chrome extension from the Chrome Web Store if you do not have it yet.
3. Connect it. Open Chrome, click the Claude extension icon, and connect it to your account. Claude can now open tabs and navigate for you.

Log into your airline and hotel accounts in Chrome before you ask Claude to book. That lets it see your real miles balances, status rates, and member-only prices that only show when you're signed in.

Claude pauses before spending money or points. It will show you the final total, the card being charged, and the details, and wait for your "Go" before it ever completes a purchase or a points transfer. You are always the one who says yes.

This is the technique that separates people who "have points" from people who fly business class for almost nothing. Your project does it automatically, but here is what it is doing so you can follow along.

What transferable points are. Points from cards like American Express, Chase, Capital One, Citi, and Bilt are flexible. You can move them to that card's airline and hotel partners. The same flight can cost wildly different amounts depending on which program you book it through, so moving your points to the right partner can cut the cost dramatically.

The method (what Claude runs for you):

1. Find the award. Claude finds the exact flight or hotel you want to book with points.
2. Price it by partner. It checks which partner program books that award for the fewest points, plus the current transfer ratio and any active transfer bonus.
3. Confirm the seat. It confirms the award seat/room is actually available to book right now.
4. Transfer, then book. Only then do you transfer and immediately book, because transfers can't be undone.

The one rule that saves you: never transfer points "just in case." Transfers are one-way and permanent. Confirm the exact award is bookable FIRST, then transfer, then book it immediately. Your project is told to always work in that order.

Transfer partners, ratios, and bonuses change often, and programs come and go. That's why the project looks up the current details in the moment instead of trusting a saved list. It also watches for transfer bonuses, which can stretch your points 20 to 40 percent further for a limited time.

Now the easy part. Give Claude the trip. It already has your profile and Points Bank, so it comes back with the smartest way to book it, points and all, with the math shown.

I want to go to [DESTINATION] from [DATES]. Use my profile and my current Points Bank to find the smartest way to book this. Show me the math (cash vs points, cents-per-point), the recommended plan plus 1-2 alternatives, any transfers required (with the live ratio and any bonus), and wait for my 'Go' before you book or transfer anything.

After you approve, Claude gives you one clean confirmation, with your points updated at the bottom.

Drop these into the same project any time. It already knows you.

Trip prep brief (run after booking):

Build a one-page trip prep brief for my [CITY] trip [DATES]: weather + packing list, 3 restaurant picks near my hotel with walking times, how to get from the airport, what I might forget, money/tipping, and one non-touristy local thing. Under 500 words.

Price-drop monitor (set as a daily scheduled task):

Every day until 24 hours before departure, check the current price of my booked flight [AIRLINE/FLIGHT/DATE/CABIN] vs what I paid ($[AMOUNT]). If it dropped, tell me the savings and exactly how to rebook or claim credit. If not, just say 'no change'.

Post-trip review (updates your Points Bank + profile):

I'm back from [CITY]. Pull this trip from our history and give me: total cost, points spent and earned (and their dollar value), progress toward my next status tier, what I'd do differently, and any profile updates. Then update my Points Bank.

Emergency card (before international trips):

Make a one-page emergency card for [COUNTRY/CITY]: local emergency number, nearest US embassy + hours, nearest hospital with English staff, my airline's rebooking line, backup flights/hotels if things fall through, and key phrases in the local language.

1. Create project. Cowork > Projects > New Project > 'Travel Agent'
2. Paste the Brain. Drop the Project Brain into the project Instructions
3. Get interviewed. Say 'interview me'; answer, incl. your real point balances
4. Connect Chrome. Ask Claude to walk you through it, or add the Chrome connector
5. Drop in a trip. 'Best way to use my points to get to [place] on [dates]?'
6. Approve + confirm. Say 'Go'; after booking, confirm 'yes' so it updates your points

Give real point balances in the interview so the Points Bank is accurate. Always confirm "yes, I booked it" so your balances stay current. Let Claude confirm the award seat BEFORE any transfer, transfers are permanent. Stay logged into your loyalty accounts in Chrome. And nothing is ever bought or transferred without your explicit "Go."

1. Build the Cowork project and paste in the Brain
2. Run the interview with your real balances
3. Connect Chrome
4. Ask it to plan your next real trip with your points
5. Approve, confirm, and let it keep your Points Bank current