What This Is
The plan · 4 steps
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.
What You Need
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.
How the Setup Flows
Create the Cowork Project
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.
Paste In The Project Brain
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
Project Brain, Part 2: The Points Bank
Project Brain, Part 3: Points + Transfer Strategy
Project Brain, Part 4: Booking Rules + Output
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.
Connect Chrome (Claude Walks You Through It)
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.
Claude will check, and if Chrome is not connected, guide you through these:
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.
The Points Transfer Playbook
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):
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.
Drop In A Trip
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.
After you approve, Claude gives you one clean confirmation, with your points updated at the bottom.
Bonus Prompts To Keep Handy
Drop these into the same project any time. It already knows you.
Trip prep brief (run after booking):
Price-drop monitor (set as a daily scheduled task):
Post-trip review (updates your Points Bank + profile):
Emergency card (before international trips):
The One-Page Cheat Sheet
The Rules That Make It Work
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."