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.

install
source · Clone the upstream repo
git clone https://github.com/borski/travel-hacking-toolkit
Claude Code · Install into ~/.claude/skills/
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"
manifest: skills/trip-planner/SKILL.md
source content

Trip 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:

ParameterExampleRequired
OriginSFOYes
DestinationParis / CDGYes
Departure date2026-08-11Yes
Return date2026-08-15Yes (assume one-way if not given)
Travelers2 adultsDefault: 1
Cabin classBusinessDefault: Economy
PreferencesFHR hotels, nonstop flightsOptional

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:

StrategyOutboundReturnHotel (4 nights)TotalPoints UsedCash Out of Pocket
All cash$4,200$3,800$1,200$9,2000$9,200
Flights: award, Hotel: cash$120 tax$95 tax$1,200$1,415110,000 UR$1,415
Flights: award, Hotel: FHR$120 tax$95 tax$8,284 (paid via points)$8,499110,000 UR + 828,400 MR$215
Flights: Chase portal, Hotel: Editvaries540,000 UR$0
Flights: award, Hotel: Airbnb$120 tax$95 tax$780$995110,000 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

OptionSourcePrice/PointsCurrency
Cash (lowest)Duffel$4,200
Flying Blueseats.aero55,000 + $120 taxChase UR (1:1)
Chase Portal Boostchase-travel180,000Chase UR

✈️ Return: CDG → SFO, Aug 15

OptionSourcePrice/PointsCurrency
Cash (lowest)Duffel$3,800
Aeroplanseats.aero70,000 + $200 taxChase UR (1:1)

🏨 Hotels: Paris, Aug 11-15 (4 nights)

OptionSourcePer NightTotalPointsBenefits
SO/ Paris [EDIT]Chase$639$2,555127,756 URBreakfast, $100 credit
Le Bristol [FHR]Amex$1,849$8,284828,400 MR$100 credit, breakfast, upgrade
Marriott ChampsSerpAPI$289$1,156
Airbnb: Marais 2BRAirbnb$195$780Kitchen

💰 Trip Total by Strategy

#StrategyTotal CashPointsCPPRating
1Award flights (FB+AC) + Airbnb$1,115125,000 UR6.5⭐ Best value
2Award flights + Chase Edit hotel$2,870252,756 UR2.5Good convenience
3All cash$8,1360Baseline
4Chase portal flights + Edit hotel$0487,756 UR1.7Most points
5Award flights + FHR hotel$8,599125,000 UR + 828,400 MRMixedLuxury

🎯 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.