Travel-hacking-toolkit trip-planner
Unified trip planning that combines flight comparison, hotel comparison, and points optimization into one complete trip cost analysis. Use when the user says "plan a trip" or wants the full picture for a destination.
git clone https://github.com/borski/travel-hacking-toolkit
T=$(mktemp -d) && git clone --depth=1 https://github.com/borski/travel-hacking-toolkit "$T" && mkdir -p ~/.claude/skills && cp -r "$T/skills/trip-planner" ~/.claude/skills/borski-travel-hacking-toolkit-trip-planner && rm -rf "$T"
skills/trip-planner/SKILL.mdTrip Planner
"Plan a trip to Paris Aug 11-15" answered with one complete cost breakdown.
Orchestrates
compare-flights, compare-hotels, transfer-partners, and trip-calculator into a unified trip analysis. Shows total trip cost in cash vs every available points strategy.
This is an orchestration skill. It tells the agent which skills to invoke and how to combine their outputs.
When to Use
- "Plan a trip to Paris Aug 11-15"
- "What's the cheapest way to do SFO to Tokyo for a week in September?"
- "How much would a trip to Stockholm cost in points vs cash?"
- Any request that involves both flights AND accommodation
When NOT to Use
- Flight-only comparison (use
)compare-flights - Hotel-only comparison (use
)compare-hotels - Award calendar (use
)award-calendar - "Should I use points?" without a specific trip (use
)trip-calculator
Workflow
Step 1: Parse Trip Parameters
Extract from the user's request:
| Parameter | Example | Required |
|---|---|---|
| Origin | SFO | Yes |
| Destination | Paris / CDG | Yes |
| Departure date | 2026-08-11 | Yes |
| Return date | 2026-08-15 | Yes (assume one-way if not given) |
| Travelers | 2 adults | Default: 1 |
| Cabin class | Business | Default: Economy |
| Preferences | FHR hotels, nonstop flights | Optional |
If anything is ambiguous, ask. Don't guess dates or travelers.
Step 2: Run Searches in Parallel
Launch ALL searches simultaneously. Don't wait for one to finish before starting another.
PARALLEL: 1. compare-flights: origin → destination, departure date, cabin 2. compare-flights: destination → origin, return date, cabin (if round-trip) 3. compare-hotels: destination, checkin = departure, checkout = return
Each of these internally runs their own parallel sub-searches (Duffel, Ignav, seats.aero, Chase, Amex, SerpAPI, Trivago, LiteAPI, Airbnb, etc).
Step 3: Combine into Trip Cost Matrix
Build a table showing total trip cost for each strategy.
For each booking strategy, calculate total = outbound + return + hotel:
| Strategy | Outbound | Return | Hotel (4 nights) | Total | Points Used | Cash Out of Pocket |
|---|---|---|---|---|---|---|
| All cash | $4,200 | $3,800 | $1,200 | $9,200 | 0 | $9,200 |
| Flights: award, Hotel: cash | $120 tax | $95 tax | $1,200 | $1,415 | 110,000 UR | $1,415 |
| Flights: award, Hotel: FHR | $120 tax | $95 tax | $8,284 (paid via points) | $8,499 | 110,000 UR + 828,400 MR | $215 |
| Flights: Chase portal, Hotel: Edit | — | — | — | varies | 540,000 UR | $0 |
| Flights: award, Hotel: Airbnb | $120 tax | $95 tax | $780 | $995 | 110,000 UR | $995 |
Step 4: Calculate Value Scores
For each strategy, compute:
Points value = (all-cash total - cash out of pocket) / total points used × 100
This tells you the CPP you're getting across the whole trip, not just one component.
Example:
"Flights: award + Hotel: Airbnb" All-cash equivalent: $9,200 Cash out of pocket: $995 Points saved: $9,200 - $995 = $8,205 Points used: 110,000 UR Trip CPP: $8,205 / 110,000 × 100 = 7.5 cpp
Step 5: Present the Trip Plan
Trip: SFO → Paris, Aug 11-15, 2 adults, Business Class
✈️ Outbound: SFO → CDG, Aug 11
| Option | Source | Price/Points | Currency |
|---|---|---|---|
| Cash (lowest) | Duffel | $4,200 | — |
| Flying Blue | seats.aero | 55,000 + $120 tax | Chase UR (1:1) |
| Chase Portal Boost | chase-travel | 180,000 | Chase UR |
✈️ Return: CDG → SFO, Aug 15
| Option | Source | Price/Points | Currency |
|---|---|---|---|
| Cash (lowest) | Duffel | $3,800 | — |
| Aeroplan | seats.aero | 70,000 + $200 tax | Chase UR (1:1) |
🏨 Hotels: Paris, Aug 11-15 (4 nights)
| Option | Source | Per Night | Total | Points | Benefits |
|---|---|---|---|---|---|
| SO/ Paris [EDIT] | Chase | $639 | $2,555 | 127,756 UR | Breakfast, $100 credit |
| Le Bristol [FHR] | Amex | $1,849 | $8,284 | 828,400 MR | $100 credit, breakfast, upgrade |
| Marriott Champs | SerpAPI | $289 | $1,156 | — | — |
| Airbnb: Marais 2BR | Airbnb | $195 | $780 | — | Kitchen |
💰 Trip Total by Strategy
| # | Strategy | Total Cash | Points | CPP | Rating |
|---|---|---|---|---|---|
| 1 | Award flights (FB+AC) + Airbnb | $1,115 | 125,000 UR | 6.5 | ⭐ Best value |
| 2 | Award flights + Chase Edit hotel | $2,870 | 252,756 UR | 2.5 | Good convenience |
| 3 | All cash | $8,136 | 0 | — | Baseline |
| 4 | Chase portal flights + Edit hotel | $0 | 487,756 UR | 1.7 | Most points |
| 5 | Award flights + FHR hotel | $8,599 | 125,000 UR + 828,400 MR | Mixed | Luxury |
🎯 Recommendation:
Award flights via Flying Blue (out) + Aeroplan (return) = 125,000 Chase UR for $8,000 worth of business class flights. That's 6.4 cpp. Excellent.
For the hotel: Chase Edit SO/ Paris gives breakfast + $100 credit for $2,555 (or 127,756 UR at 2.0 cpp via boost). The Airbnb is cheapest at $780 but no breakfast or hotel amenities.
Best overall: Award flights + Airbnb if you want max savings. Award flights + Chase Edit if you want the hotel experience with benefits.
Step 6: Source Status
Always report which sources succeeded and which failed:
✅ Duffel: 45 outbound, 38 return ✅ Ignav: 40 outbound, 35 return ✅ Seats.aero: 12 award options outbound, 8 return ✅ Chase Travel: 300 outbound flights, 21 hotels ✅ Amex Travel: 292 outbound flights, 17 hotels ✅ SerpAPI: 25 hotels ✅ Trivago: 30 hotels ✅ LiteAPI: 22 hotels ✅ Airbnb: 18 listings ✅ Google Flights: 52 outbound ⏭️ Southwest: skipped (no SFO-CDG service)
Error Handling
NEVER fail silently. If any sub-search fails, note it and continue with what you have.
If flights fail but hotels succeed (or vice versa), present what you have and note the gap:
❌ Seats.aero: API timeout. Award flight pricing unavailable. Trip totals shown are cash-only and portal-only. Retry seats.aero for award options.
If ALL sources fail for one component, say so:
❌ All hotel sources failed. Cannot calculate trip total. Fix hotel search, then rerun.
Limitations
- Round-trip cash prices from Duffel/Ignav may be cheaper than two one-ways. Note when this is the case.
- Award pricing is one-way. The combined outbound + return award cost is the correct comparison against a round-trip cash fare.
- Hotel pricing may vary between portal and direct booking. Note significant differences.
- Chase portal 1.5x multiplier is applied at checkout, not in the listing. The skill adjusts automatically.
- Trip totals are estimates. Taxes, fees, and exchange rates can change actual booking costs.