Agent skill

Booking Guidance

by borski in borski/travel-hacking-toolkit

Step-by-step guidance for booking award flights. An agent skill from borski/travel-hacking-toolkit.

MITAuto-check passed

Install Booking Guidance

skills CLI
$ npx skills add borski/travel-hacking-toolkit --skill booking-guidance -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install borski/travel-hacking-toolkit booking-guidance --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/borski/travel-hacking-toolkit.git skills-src && mkdir -p .claude/skills && cp -r skills-src/plugins/travel-hacking-toolkit/skills/booking-guidance .claude/skills/booking-guidance && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
booking-guidance
GitHub stars
688
Token cost
~2.1k tokens
SKILL.md length
1,166 words
Files
1
Skills in repo
46
Repo updated
First seen
Licence
MIT

At a glance

Step-by-step guidance for booking award flights. An agent skill from borski/travel-hacking-toolkit.

  • Works in 5 steps: Find availability (Seats.aero, airline… → Verify the program you want to book… → If transferring points: get a HOLD on… → …
  • SKILL.md covers Program Fee Profiles, General Booking Flow, Critical Rule: Never Transfer… and Phone Numbers for Major Programs, plus 4 more sections
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

Booking Guidance is an agent skill from borski/travel-hacking-toolkit. Step-by-step guidance for booking award flights. Covers the hold-before-transfer rule, phone numbers for major programs, and partner award booking workflows.

Its SKILL.md is about 2.1k tokens, which your agent loads only when the skill is triggered. It is a single SKILL.md file with no bundled scripts.

The repository describes itself as: AI-powered travel hacking and search with cash, points, miles, and award flights. Drop-in skills and MCP servers for Claude, Codex, and OpenCode. The licence is MIT.

Example prompts

  • “/booking-guidance”

Workflow steps

5 steps, taken from the first numbered list in SKILL.md.

  1. Find availability (Seats.aero, airline website, or MCP tool)
  2. Verify the program you want to book through shows the same availability
  3. If transferring points: get a HOLD on the award ticket FIRST, then transfer
  4. Transfer points from credit card to loyalty program
  5. Call or go online to complete the booking

What it can do on your machine

Read from SKILL.md and the folder at commit db82131. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md.

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Booking Guidance loads about 2.1k tokens when it runs. Until then it costs about 44 tokens; SKILL.md has 1,166 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~44
When it runs · the whole SKILL.md, loaded when a task matches
~2.1k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from borski/travel-hacking-toolkit at commit db82131, republished under its MIT licence (© borski). 1,166 words, ~2,141 tokens.

Download SKILL.mdSave it as .claude/skills/booking-guidance/SKILL.md (or your agent's skills folder).
name
booking-guidance
description
Step-by-step guidance for booking award flights. Covers the hold-before-transfer rule, phone numbers for major programs, and partner award booking workflows.
category
reference
summary
The booking flow, hold-before-transfer rule, phone numbers for major programs.

Booking Guidance

Finding the deal is half the battle. Telling the user how to actually book it is the other half. Every recommendation should include a booking path.

Reference data: data/alliances.json has booking details for major programs in key_booking_relationships.

Program Fee Profiles

Check this before recommending a transfer or locking in a departure city. Fees vary dramatically by program and origin airport and can add $100-700+ per person on top of the miles cost. Two things to keep in mind reading the table: (1) several programs are surcharge-free on their own metal and most partners but pass heavy surcharges on specific partners (notably British Airways metal) — the YQ column calls those out; (2) dollar figures are per direction and scale with cabin — economy surcharges are materially lower than the business-class figures shown for surcharge-heavy metal. Rows marked ⚠️ are high-surcharge programs that often lose to cash.

ProgramYQ Surcharge?Typical fees/ppNotes
Aeroplan (Air Canada)No$50-100No YQ pass-through on Star Alliance partners. Low fees. Best for LH/LX/UA awards.
Flying Blue (AF/KLM)Yes~$250-400/way economy, ~$489-600/way business, ex-CDGAF passes full fuel surcharge; France adds heavy departure tax. Worst from Paris.
United MileagePlusNo$50-100No YQ on most partners.
Virgin AtlanticYes (on VS metal)Cabin-dependent: ~$150-300/way economy, ~$500-700/way Upper Class; low on Delta metalSurcharges scale with cabin. Delta metal carries surcharges US↔UK specifically.
Turkish Miles & SmilesNo on UA/Turkish metal; YES on Lufthansa Group (LH/LX/OS/SN)$20-50 (own/UA metal)Extremely low on own/UA metal. Book by phone (online unreliable). Dec 2025 devaluation.
British Airways AviosYes~$200-400/way economy, ~$400-700/way business, BA long-haul metalNotorious surcharges on BA metal. Use short-haul, or partner metal (AA/Alaska/Qatar), instead.
American AAdvantageNo on own metal + most partners; YES on British Airways & Iberia$50-75 base; on BA/IB metal ~$200-400/way economy to $400-700+/way businessSurcharge-free on JAL/Cathay/Qatar. Route partner awards away from BA/Iberia metal.
Alaska / Atmos RewardsNo on own metal + most partners; YES on British Airways, Icelandair, Hainan$25-75 base; on BA metal ~$150-400/way economy up to ~$1,000/way premiumRenamed from Mileage Plan (Aug 2025). Surcharge-free on Cathay/JAL/Qantas/Condor/Fiji.
Avianca LifeMilesNo~$25/ticketNo-YQ Star Alliance program. Predictable total even on ANA/Lufthansa/Swiss metal.
Iberia Plus (Avios)Low (far less than BA)~$150-200 RT transatlantic businessThe transatlantic Avios sweet spot: MAD-US business ~40.5K-59K Avios/way with modest surcharges.
JAL Mileage BankNo on JAL metalfrom ~$20Cheap distance-based partner chart. Partner metal (e.g. BA) may add YQ.
Qatar Privilege Club (Avios)No fuel surcharge on Qatar metal~$30-100 per-segment feeExcellent Qsuites value. Per-segment cash fee returned in 2025.
Delta SkyMilesNoNo award feesDynamic award pricing is the real cost, not fees.
⚠️ ANA Mileage ClubYes — heavy~$95-185/way US-Japan YQRound-trip booking only; no awards within 96h of departure.
⚠️ Cathay / Asia MilesYesHigh on long-haul; hiked again in 2026Passes full carrier-imposed surcharges.
⚠️ Emirates SkywardsYes — heavyAmong the highest YQ of any programSurcharges often kill the redemption vs cash.

Key rule: If the trip ends in Paris or London, or routes on Air France / BA / Virgin / Emirates metal, factor $300-700/pp per direction in fees before comparing programs. A 40K Flying Blue award from CDG often costs more in cash fees than a 50K Aeroplan award from FRA. When a program passes surcharges only on specific partners (AA/Alaska on BA metal, Turkish on Lufthansa Group), route around that metal to keep fees low.

General Booking Flow

  1. Find availability (Seats.aero, airline website, or MCP tool)
  2. Verify the program you want to book through shows the same availability
  3. If transferring points: get a HOLD on the award ticket FIRST, then transfer
  4. Transfer points from credit card to loyalty program
  5. Call or go online to complete the booking
Show full SKILL.md (546 more words)Show less

Critical Rule: Never Transfer Without a Hold

Transfers are instant with most programs but IRREVERSIBLE. If availability disappears between the transfer and the booking, points are stuck in the loyalty program.

The right order:

  1. Find the award and put it on hold (24-72 hours typically) through the booking program
  2. THEN transfer points from the credit card
  3. THEN complete the booking against the held space

Critical caveat: hold rules vary widely and change. Always check the award-holds skill (data file data/award-holds.json) for current per-program rules. As of April 2026: AA holds 24h online (free), Lufthansa M&M 5 days, Flying Blue 3 days ($25 phone fee at ticketing), Cathay Asia Miles 2 days ($39 phone fee), Turkish 2 days, Virgin Atlantic 1-2 days (free, phone), Singapore agent-discretionary. Programs that DO NOT allow holds: United, Alaska, Delta, BA, Aeroplan, ANA, Qatar, Korean. The "hold first, transfer second" pattern works wherever a hold is available.

When holds aren't available, transfer in small batches if you're confident the space will hold (high seat counts, low-popularity dates), or accept the risk. Never transfer your full balance speculatively.

Phone Numbers for Major Programs

Some awards must be booked by phone. Memorize or save these.

ProgramPhoneOnline Booking?
Virgin Atlantic (ANA awards)1-800-365-9500No (ANA must be by phone)
United MileagePlus1-800-864-8331Yes (united.com)
Aeroplan1-888-247-2262Yes (aircanada.com)
Turkish Miles&Smiles1-800-874-8875Yes (turkishairlines.com)
Korean Air SKYPASS1-800-438-5000No (partner awards by phone)
Flying Blue1-800-237-2747Yes (stopovers by phone)
AAdvantage1-800-882-8880Yes (aa.com)
Japan Airlines1-800-525-3663No (find space on ba.com or qantas.com, call JAL to book)
Iberia AviosN/AYes (iberia.com)
Qatar Privilege ClubN/AYes (qatarairways.com)
HyattN/AYes (hyatt.com or app)

When Phone Bookings Are Required

A partner award that's "hidden" (not bookable online) often requires a phone agent. Common cases:

  • ANA First/Business via Virgin Atlantic: Must call. Agent searches space manually.
  • JAL via Alaska or AAdvantage: Find space on ba.com (proxy), then call to book.
  • Korean Air partner awards: Skypass partner awards are phone-only.
  • Stopovers on most programs: Online tools rarely allow stopovers. Call.

Tips for Phone Bookings

  • Have flight numbers, dates, and class ready. Don't ask the agent to "look around."
  • HUCA (Hang Up, Call Again) is a real strategy. Some agents are better than others. If one says "no space," try another.
  • Confirm the fare before agreeing. Some programs charge surcharges that wreck the cpp math.
  • Get a booking reference (PNR). Verify the ticket on the operating airline's site within 24 hours.

Saver Inventory Verification

Many partner programs only see "saver" inventory on the operating carrier. If you find space on the operating airline's site but the partner program shows nothing, check the fare class. Saver classes are X (economy), I (business), O (first) on United. If the carrier only has standard or anytime class open, partners can't book it.

See the cabin-codes skill for the full mapping.

Status Effects on Booking

Elite status with the booking program (or alliance partner) often unlocks longer hold windows, waived close-in booking fees, and priority on phone bookings. If the user has elite status, mention which benefits apply. If they don't and the question of getting status comes up, load the status-match skill — it covers the lifetime restrictions that punish wasted matches and the renewable card-based alternatives.

© borski, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

Just SKILL.md in plugins/travel-hacking-toolkit/skills/booking-guidance of borski/travel-hacking-toolkit.

Open the folder on GitHubat commit db82131

Compare with similar skills

Booking Guidance next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

Booking Guidance compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Booking Guidance this skillborski/travel-hacking-toolkit688—~2.1kAutomated safety check: PassMIT
Flightsasgeirtj/system_prompts_leaks69k—~2.1kAutomated safety check: PassCC0-1.0
Flight Booking AItourmind-com/Tourmind-Booking-Skills1.8k—~11kAutomated safety check: PassMIT
Flightscodewhale-hq/Codewhale41k—~258Automated safety check: PassMIT
Day Booksickn33/agentic-awesome-skills47k1 repos~7kAutomated safety check: PassMIT
BookingsBuilderIO/agent-native7.1k—~345Automated safety check: PassNone

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Questions about Booking Guidance

What does Booking Guidance do?

Step-by-step guidance for booking award flights. An agent skill from borski/travel-hacking-toolkit. Booking Guidance is an agent skill from borski/travel-hacking-toolkit. Step-by-step guidance for booking award flights.

How do I install Booking Guidance in Claude Code?

Run `npx skills add borski/travel-hacking-toolkit --skill booking-guidance -a claude-code`. Or copy the skill folder (plugins/travel-hacking-toolkit/skills/booking-guidance in borski/travel-hacking-toolkit) into .claude/skills/booking-guidance in your project. Claude Code loads it when a task matches its description.

How do I install Booking Guidance in Codex?

Run `npx skills add borski/travel-hacking-toolkit --skill booking-guidance -a codex`. Or copy the skill folder (plugins/travel-hacking-toolkit/skills/booking-guidance in borski/travel-hacking-toolkit) into .agents/skills/booking-guidance in your project. Codex loads it when a task matches its description.

Can I use Booking Guidance in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add borski/travel-hacking-toolkit --skill booking-guidance -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/booking-guidance, .gemini/skills/booking-guidance, .github/skills/booking-guidance and .opencode/skills/booking-guidance in your project.

What does Booking Guidance need to run?

SKILL.md names no scripts, command-line tools or credentials: Booking Guidance is instructions for the agent only.

Does Booking Guidance access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Booking Guidance safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Booking Guidance use?

Booking Guidance is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Booking Guidance use?

About 2.1k tokens (SKILL.md is roughly 8.6k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.

What are the alternatives to Booking Guidance?

Skills that share tags, products or a category with Booking Guidance: Flights (asgeirtj/system_prompts_leaks, 69k stars), Flight Booking AI (tourmind-com/Tourmind-Booking-Skills, 1.8k stars), Flights (codewhale-hq/Codewhale, 41k stars) and Day Book (sickn33/agentic-awesome-skills, 47k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Booking Guidance?

borski (a GitHub user) maintains it in borski/travel-hacking-toolkit, which has 688 GitHub stars. The repository holds 46 skills in this directory. The repository was last updated on October 5, 2026.

Source: borski/travel-hacking-toolkit on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.