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A free guide by Mariah Brunner ↗ INSTAGRAM ↗ TIKTOK

The Claude
Flight-Booking Skill

Claude can record your screen and turn it into a reusable Skill. Here’s the exact flight Skill to steal, plus how to record your own.

Claude can watch your screen while you do a task, listen to you talk through it, and turn the whole thing into a Skill it can run again. You teach it once, and it follows your rules every time after that.

Here are both halves: my flight-booking Skill to download, and how to record your own. For context, Boris Cherny, who built Claude Code, put his flight preferences into his Claude Cowork instructions and had it book 8 flights and 5 hotels while he worked on something else. This is your version of that.

How To Record A Skill

Record a skill lives in Cowork in the Claude desktop app for Mac. It works on Pro, Max, Ultra and Team plans (not Free, Enterprise or Windows yet).

  1. Update to the latest Claude for Mac and open Cowork.
  2. First time only, grant the macOS Accessibility and Screen Recording permissions Claude asks for.
  3. Click + in the message box and choose Record a skill. (Or go to Customize, which newer versions call Plugins, then Skills, click Add and pick Record your screen.) Click Start recording and leave your mic on.
  4. Do the task the way you normally would and talk through your reasoning, like why you skip a step or how you pick between two options. That’s the part Claude can’t see.
  5. Click Done. Claude proposes a Skill. Expand Content to read it, then click Save.

Recordings run up to about ten minutes, so keep each one to a single, clean task. Close anything private first, and never type a password on camera.

Claude doesn’t keep the video or audio. It does save screenshots from the session inside that Cowork task, and deleting the task removes them.

My Flight Booking Skill

Here’s the actual Skill. Download the ZIP, or copy it below, then fill in the brackets with your real preferences. This is what turns "find me flights to Tokyo in October" into Claude already knowing exactly how you decide.

↓ Download the skill (.zip)
flight-booker / SKILL.md
--- name: flight-booker description: Find, compare and book flights and hotels using my saved travel rules. Use whenever I ask to find, compare or book flights, hotels or a trip. --- # Flight Booker You are my travel assistant. Your job is to find the trips that fit my rules, show me a short shortlist, and only book after I say yes. Fill every [bracket] below with my real details before using this skill. ## Who I am - Name exactly as it appears on my ID: [full name] - Home airport(s): [e.g. SEA, plus PDX if it's cheaper] - Known Traveler / TSA PreCheck number: [number, or "ask me for it at checkout"] - Loyalty numbers and status: [airline + hotel programs] ## How I choose flights (my rules) - Prefer NONSTOP if it's within $200 of the cheapest option. - Preferred airlines: [e.g. Alaska, then United]. Avoid: [e.g. Spirit, Frontier]. - Never book an overnight layover. Minimum connection 60 minutes, maximum 1 stop. - Prefer MORNING departures. Avoid red-eyes. - Seat: aisle, forward cabin, never a middle seat. - Cabin: economy under 4 hours, premium or business over 6 hours. - Hard nevers: no basic economy, no more than 1 stop, no red-eyes. ## How I choose hotels - Preferred chains (where I have status): [chains]. Area: [neighborhood or near the venue, walkable]. - Budget ceiling: [$X per night]. Prefer refundable rates. Breakfast included if possible. ## Budget and priorities - Trip budget ceiling: [$X total]. - Optimize in this order: 1) total travel time, 2) price, 3) loyalty earning. ## How to work 1. If anything about the trip is unclear (dates, flexibility, who is traveling), ask me first, in one short message. 2. Search options that fit my rules. If nothing fits, say which rule you had to bend and why. 3. Show me a shortlist of 2 to 4 options in a table: airline or hotel, price, times, stops, cancellation or change policy, and one line on why each made the cut. 4. WAIT for me to pick before you book anything. 5. Before final payment, show me the full total (taxes, bag and seat fees included) and WAIT for my explicit "yes." 6. Never enter payment or charge anything without my confirmation. Never save my full card number, passport number or passwords in this file or in chat. 7. After booking, give me a summary: confirmation numbers, times in local time zones, and anything I still need to do (check-in, seat selection). ## Example Me: "Find me the best flights to Tokyo in October, the 8th to the 16th." You: apply the rules above, then show a shortlist and ask me which one to book.

Two Safety Gates

Never let an AI spend money without you. This Skill makes Claude stop twice: once to confirm which option to book, and again before final payment. Keep card and passport numbers out of the file.

Install It
  1. Fill in your brackets first. Unzip, edit SKILL.md with your details, then zip the flight-booker folder again. Or install it as is and ask Claude to update it with your preferences.
  2. Turn on code execution. In Claude, go to Settings, then Capabilities, and turn on Code execution and file creation (newer layouts call it Create and edit files). Skills need it, and they work on every plan, including Free. On Team or Enterprise, your admin controls this.
  3. Upload it. Go to Customize (or Plugins), then Skills. Click +, then Create skill, then Upload a skill, and pick the ZIP.
  4. Switch it on in your skills list.

Claude reads the Skill’s description and uses it on its own whenever you ask about flights or hotels. To actually book, run it in Cowork, which can open your browser and click through the sites. In regular chat it can still research and build your shortlist.

In Claude Code, a Skill is a folder in ~/.claude/skills/. One heads-up: Skills don’t sync across surfaces, so a Skill you add in the Claude app isn’t automatically in Claude Code. More in the Claude help center and the Agent Skills docs.

Want the deeper walkthrough on the booking itself? I covered how to book flights with Claude here.