Imagine exploring Paris, Rome, and Athens on a single, seamless trip. Or maybe you're a digital nomad planning to work from Lisbon, then Bali, then Mexico City. Crafting a journey with multiple stops can seem complex, but it's an amazing way to see more of the world. With the right strategies, you can book multi-destination flights that save you both time and money. You’ll be delighted to learn that going to multiple destinations on holiday may be more cost-efficient than staying in one place. You'll discover the secrets to finding the best routes, using powerful search tools, and combining different types of tickets for maximum value. Get ready to unlock your next big adventure and long-lasting memories!

Why Book Multi-Destination Flights?

Booking a multi-city itinerary offers huge advantages over separate one-way tickets. It's all about being strategic.

  • Save Money: A single multi-city ticket is often far cheaper than booking individual flights for each leg of your journey.
  • Save Time: You avoid backtracking to your original arrival city, giving you more precious time to explore your destinations.
  • Greater Convenience: Manage your entire trip under one booking reference, which simplifies check-in and luggage handling.
  • Unlock More Destinations: See places you might have otherwise skipped by building them into one cohesive trip.

Key Ticket Types: Open-Jaw and Multi-City

Understanding the lingo is the first step. Two powerful options are open-jaw and multi-city tickets.

Open-Jaw Tickets

An open-jaw itinerary is when you fly into one city and fly home from another. For example, flying from New York to London, then making your own way to Paris (by train, perhaps) and flying home from Paris to New York. This is perfect for road trips or regional tours where you don't want to circle back.

Multi-City Tickets

A multi-city ticket includes three or more flights in one booking. For instance, you could book a flight from Chicago to Tokyo, then Tokyo to Bangkok, and finally Bangkok back to Chicago. This is the ultimate tool for world travelers and anyone planning an extensive tour.

Powerful Tools for Finding the Best Flights

Forget simple airline searches. To find the best multi-city deals, you need to use more advanced tools.

  • Google Flights: The "Multi-city" tab on Google Flights is the most user-friendly tool for building complex trips. Its calendar view helps you quickly see how changing dates affects the price of each leg.
  • Skyscanner: Similar to Google Flights, Skyscanner lets you search for multi-city routes. Its "Everywhere" feature can also inspire new stops for your journey if you're flexible.
  • ITA Matrix: This is the powerful software that powers Google Flights and many other search engines. While you can't book directly on ITA Matrix, it offers incredibly advanced filtering options. You can specify airlines, alliances, and connections to find the perfect fare, then provide the details to a travel agent or replicate the search on the airline's website.

Advanced Strategies for Expert Travelers

Ready to take your flight booking skills to the next level? These strategies can uncover incredible value, but they require careful planning.

The Hub Strategy

Airlines operate out of major hubs (e.g., Delta in Atlanta, British Airways in London). Flying into and out of these hubs can often result in lower fares. When planning your multi-city trip, consider routing your journey through major airline hubs to access more flight choices and competitive pricing.

Leveraging Alliances and Stopovers

Major airlines are grouped into alliances like Star Alliance, oneworld, and SkyTeam. Booking with airlines in the same alliance can make your journey smoother, especially for baggage transfers.

Even better, some airlines offer free or low-cost stopovers. This means you can add an extra city to your itinerary for little to no extra cost. Icelandair allows stopovers in Reykjavik, and Turkish Airlines offers them in Istanbul. It's like getting a bonus vacation!

Mixing and Matching Airlines

Don't be afraid to combine flights from different carriers. You might fly a legacy airline like United across the Atlantic and then use a low-cost carrier (LCC) like Ryanair or easyJet for short hops around Europe.

Important Note: When you mix and match airlines on separate tickets, be mindful of baggage. LCCs often charge extra for checked and even carry-on bags. Also, ensure you leave plenty of time between flights, as you'll have to collect your luggage and check in again.

Positioning Flights

Sometimes, the best deal for a long-haul flight isn't from your home airport. A "positioning flight" is a separate, cheap ticket you book to get to a city with better international fares. A flight from New York to Singapore might be $1500, but a flight from Los Angeles is only $800. You could book a cheap flight from New York to LA to catch a better deal and still save hundreds.

Using Miles and Points

Frequent flyer miles are one of the best ways to book multi-city trips.

  • Sweet Spots: Award charts have "sweet spots"—routes that offer amazing value for your points. Research these for your desired destinations.
  • Transfer Partners: Credit card points from programs like Chase Ultimate Rewards or American Express Membership Rewards can be transferred to dozens of airline partners. This gives you the flexibility to book with whichever airline has the best availability.
  • Award Search Tools: Use services like point.me or seats.aero to search for award availability across multiple airlines at once.

A Word of Caution: Hidden-City and Throwaway Ticketing

You may have heard of "hidden-city" ticketing (booking a flight with a layover and ending your journey there) or "throwaway" ticketing (booking a round-trip but only using the outbound flight). These tactics can sometimes save money, but airlines strictly prohibit them. If you're caught, the airline could cancel the rest of your ticket, void your frequent flyer miles, or even ban you from flying with them. It is generally not worth the risk.

Sample Itineraries: Putting It All Together

Example 1: The European Tour (Cash Booking)

  • Goal: Visit London, Rome, and Paris from Boston.
  • Logic: Use an open-jaw ticket to avoid backtracking. Fly into the northernmost city (London) and out of a convenient hub (Paris).
  • Itinerary:
    1. Book an open-jaw flight: Boston (BOS) -> London (LHR) and Paris (CDG) -> Boston (BOS).
    2. Book a separate, cheap one-way flight or train ticket from London to Rome.
    3. Book another one-way from Rome to Paris.
  • Why it works: You save time and money by not needing to fly back to London for your return flight.

Example 2: The Southeast Asia Adventure (Points Booking)

  • Goal: Visit Japan, Vietnam, and Thailand from San Francisco using points.
  • Logic: Leverage an airline alliance and a flexible points currency.
  • Itinerary:
    1. Transfer Chase points to a Star Alliance partner like Air Canada Aeroplan.
    2. Book a multi-city award ticket: San Francisco (SFO) -> Tokyo (NRT).
    3. Add a second leg: Tokyo (NRT) -> Hanoi (HAN).
    4. Add a third leg: Bangkok (BKK) -> San Francisco (SFO).
    5. Book a separate, cheap flight on a local LCC from Hanoi to Bangkok.
  • Why it works: You can book most of the long-haul flights on one award ticket for a fixed number of points, saving cash for experiences on the ground.