Whether you’ve got eyes on a Eurotrip or want to go coast to coast in the US, figuring out flight details can be tricky when you want to visit a few destinations. This multi-city trip planner will break down your options for booking flights so you can decide whether to get individual one-way tickets or buy it all in one go as a single multi-city itinerary.

When you're planning a trip with multiple stops, you might think the only option is to book several one-way flights. But there's a lesser-known alternative: the multi-city itinerary. This is a single reservation that includes all the flights on your route, allowing you to fly into one city and return home from another. Each type of booking has its pros and cons, so let’s dive into the details to figure out which is right for your vacation. 

Most flight search engines, like Skyscanner, and individual airlines have three flight search options: one-way, roundtrip, and multi-city. When you select multi-city, you’re able to add a number of legs to your flight. Skyscanner, for example, lets you add up to six legs, meaning you can travel on six different flights under one reservation. This option not only simplifies the search process, but can often be less expensive than booking the same flights as individual one-way tickets. That may not always be the case, but if you want to save money, you should always check. 

The biggest advantage to using Skyscanner for a multi-city flight search is that you will see a variety of results with itineraries that use a single carrier, multiple carriers within an airline alliance, or a mix of carriers that may not have a common affiliation. Whereas if you do a multi-city search on an airline’s website, like United, you will only get search results that include that airline, which limits your choices, especially if they don’t have a local partner at one of your destinations. By being open to mixing and matching airlines, you’ll have access to a wider range of flight options and pricing. 

The ease of booking and potential savings are big positives when it comes to multi-city reservations. The downsides? A flight booking that has multiple airline tickets will likely also have a mix of policies for changes and cancellations. It’s also possible that if you miss one flight, the rest of your itinerary will be voided. If either of these are potential concerns for you, just contact the airline or booking platform’s customer service line ahead of time to understand how the process would work. This can put you at ease because it may be a lot simpler than you think. The other potential drawback is that you’ll have less flexibility for open-ended travel, but this is really only applicable if you don’t know your return date.

One-way flight searches are simple and straightforward. You can book on any airline, regardless of alliance, and choose the airport, travel dates, and fare class that works best for your trip. The only hassle is that you’ll need to perform multiple flight searches to look up all the routes for your trip. This can take much longer than using the multi-city flight search tool. But if you want to compare one-way flights vs multi-city reservations based on price, you’ll need to perform both types of searches anyway.

The biggest advantage to booking individual tickets is that they will not be tied to a single itinerary and therefore won’t affect one another should you change, cancel, or miss a flight. But if your trip doesn’t have any mishaps, that probably won’t matter.

Need an example of how this all works? Let's take a look at an 11-day international adventure we put together. It starts in Chicago, with a flight to Quito, Ecuador, then zips over to Lima, Peru, before a final flight back home to Chicago. We'll show you how the numbers shake out for this trip for a solo traveler and a family (two adults, two kids) reserving economy tickets at the cheapest price possible.

Solo traveler

Family of 4

As you can see in the comparisons above, the total costs are not too far off from one another. In the end, if you can find a multi-city itinerary that works with your date, time, and airline preferences, you can save a lot of time by just running one search instead of multiple. However, if you're set on booking a series of one-way tickets but just waiting for better prices, we recommend setting up a Price Alert for each route. You'll get notified as soon as airfare drops so you can snag a good deal before the price changes again.

Flight searches for Chicago to Quito, Quito to Lima, Lima to Chicago, and the multi-city itinerary comparisons were performed on Sept. 8, 2025. All above information was accurate as of that date.

Final thoughts: Multi-destination flights and bookings

Booking a single multi-city itinerary is a game-changer when it comes to saving time, and sometimes it can also be the most budget-friendly option. So, before your next trip, head to Skyscanner’s flight search to quickly compare both options: you'll be glad you did.