Trip Planner

Companion reference skills. Load these for deeper context:

• flight-search-strategy — full search workflow and source priority
• lessons-learned — Seats.aero workflow and common failure modes (load before any award search)
• points-valuations — CPP rules, opportunity cost
• partner-awards — reachability through alliance + bilateral partnerships
• award-sweet-spots — flag legendary redemptions
• booking-guidance — booking flow + phone numbers + the "hold before transfer" rule
• transfer-bonuses — live current transfer bonuses (weekly refresh) before recommending any transfer
• stopovers — per-program stopover rules; can turn a one-trip plan into a multi-city itinerary at no extra mileage cost
• award-holds — per-program hold rules; affects transfer timing decisions
• round-the-world — when the trip request implies 3+ stops or multiple regions, RTW products may be cheaper than separate awards
• status-match — when a user mentions wanting status or asks about elite tier shortcuts; covers free direct matches, paid concierge fees, and once-per-lifetime warnings

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:

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:

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

✈️ Return: CDG → SFO, Aug 15

🏨 Hotels: Paris, Aug 11-15 (4 nights)

💰 Trip Total by Strategy

🎯 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 pricing is dynamic Points Boost (~1.5-2.0 cpp on select bookings, not a guaranteed floor). The historical static 1.5x multiplier is gone. Pull the actual quote.
• Trip totals are estimates. Taxes, fees, and exchange rates can change actual booking costs.