Multi-City Trip Planning: How to Book Open-Jaw and Round-the-World Tickets the Smart Way

Why Multi-City Trip Planning Is Different

A return ticket (A→B→A) is the simplest booking transaction in travel. A multi-city trip (A→B→C→D→A, or A→B with no return) is fundamentally more complex — more combinations, more variables and significantly more opportunity to either save or waste money through booking strategy.

The difference between a well-structured multi-city booking and a poorly structured one can easily be $300–$800 on a 3-week trip.

Understanding the Key Booking Structures

Point-to-Point Individual Tickets

Booking each flight as a separate transaction. Maximum flexibility but potentially most expensive, and no airline protection if one flight is delayed and causes you to miss the next.

Best for: Budget airline routes where individual tickets are dramatically cheaper; trips where each leg is on a different carrier with no logical combination

Open-Jaw Ticket

A return ticket where you depart from city A, arrive at city B, then depart from city C (different from B) and return to city A. Or arrive at A but return from B.

Example: London → Tokyo → fly to Bangkok → Bangkok → London

Airlines treat this as a single itinerary and price it as a return fare — often very close to the price of a simple A→A return, making it exceptional value when you plan to travel between cities within the destination region.

Open-jaw is almost always better value than two separate one-ways when flying internationally.

Circle Trip / Round Trip via Multiple Continents

A ticket that visits multiple cities and returns to the origin, booked as a single itinerary through one airline or alliance:

Example: London → Singapore → Sydney → Los Angeles → London

Major airlines allow these "circle trip" fares through their booking systems — price them on the airline's website by adding multiple stops.

Key rule: All segments must be in the same overall direction of travel (generally eastbound or westbound, not doubling back).

Round-the-World (RTW) Tickets

A special fare category offered by airline alliances (Star Alliance, Oneworld, SkyTeam) covering up to 16 destinations on a single ticket across a 12-month period.

Oneworld Explorer RTW: Price based on number of continents visited

• 3 continents: ~$2,600–$3,200 economy
• 4 continents: ~$3,500–$4,200 economy
• Business class: 2.5–3.5x economy prices

Star Alliance Round the World: Priced by mileage bands

• 26,000 miles: ~$2,500–$3,100 economy
• 34,000 miles: ~$3,100–$3,800 economy
• 39,000 miles: ~$3,700–$4,500 economy

RTW tickets make financial sense when: You plan 4–6 long-haul flights across multiple continents within 12 months. Breaking down the cost: a $3,500 RTW covering London → New York → Los Angeles → Tokyo → Bangkok → London would cost $2,800–$4,500 booked as individual flights — the RTW often wins.

RTW tickets do NOT make sense when: You want maximum flexibility to change dates (change fees apply); you plan primarily short-haul regional travel; your itinerary involves primarily one or two continents.

The Multi-City Booking Workflow

Step 1 — Map Your Rough Itinerary

Before touching any booking tool, write out your rough journey: cities, approximate dates, must-have vs flexible segments. Identify which legs are:

• Fixed: Specific dates you cannot change (events, connections to work, visa dates)
• Flexible: Arrival/departure can shift by 1–5 days for price optimisation

Step 2 — Check Multi-City Tools First

ITA Matrix is the professional-grade tool used by travel agents — it shows all possible fare combinations and routing options for complex itineraries. Note: it does not book directly; use it to find the best combination, then book through the airline or an OTA.

Step 3 — Check the Open-Jaw Option

Before booking separate tickets, check whether an open-jaw structure on a single ticket is cheaper. Search:

• London → Bangkok, return from Tokyo → London

vs.

• London → Bangkok (one way)
• Tokyo → London (one way)

The single open-jaw ticket is often within $50–$150 of the cheapest two one-ways — and includes baggage and booking protection advantages.

Step 4 — Identify Regional Legs Separately

For the inter-region segments (Bangkok → Tokyo in the example above), book separately using regional carriers:

• Southeast Asia to Japan: AirAsia X, Scoot, Jetstar
• Europe to Middle East: Flydubai, Air Arabia, Wizz Air
• Within South America: LATAM, Avianca, Copa

These regional legs are almost always cheaper booked independently with LCCs than as connecting segments on long-haul carriers.

Practical Example: 3-Week Europe to Asia Trip

Itinerary: London → Rome (5 days) → Dubai (3 days) → Bangkok (7 days) → Chiang Mai (4 days) → fly home to London

Strategy:

1. Open-jaw main ticket: London → Dubai, Bangkok → London (~£650–£850 on Emirates/Etihad/Qatar)
2. Separate budget flight: London → Rome (~£60–£90 on easyJet/Ryanair)
3. Train or budget flight: Rome → London or overland
4. Regional LCC: Dubai → Bangkok (~$120–$180 on Air Arabia + AirAsia or Flydubai)
5. Domestic Thailand: Bangkok → Chiang Mai (~$25–$45 on Thai AirAsia or Nok Air)

Total flights: £1,000–£1,250

vs. booking everything as individual one-way long-haul flights: £1,600–£2,400

Saving: £400–£1,150 through strategic booking

Common Multi-City Booking Mistakes

• Booking all legs through one carrier when better combinations exist: Alliance loyalty should not override significant price differences
• Not checking open-jaw before separate one-ways: Takes 5 minutes and saves potential $100–$300
• Ignoring ground transport between city pairs: Sometimes bus or train between nearby cities (Paris–Amsterdam, Bangkok–Siem Reap, Buenos Aires–Montevideo) is faster and cheaper than flying
• Booking too early on flexible legs: For budget airline segments, booking 6–8 weeks ahead often beats both same-week booking and very-early booking
• Forgetting baggage continuity: On self-transfer itineraries (separate tickets), you must collect and re-check bags between flights — allow minimum 2.5–3 hours for this process