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How to Book Multi Destination Flights: The Best Tools & Resources

I have a confession to make: I’m a bit of a country counter.

I aim to visit multiple countries on every international trip I take, and through all of this planning I’ve learned a few tips and tricks for finding and booking multi destination flights.

In 2019 I visited 14 countries on 3 separate trips. I’ve never relished the idea of shuttling between home and each country that I want to see on a bunch of individual, unrelated jaunts — especially with a one-year-old in tow. If that was the only way to travel the world, I’d do it in a heartbeat, but individual trips are often more expensive, more rushed and less enjoyable than long excursions.

You’re probably thinking “duh, of course I’d prefer to travel for a month at a time instead of a week…wouldn’t we all?!” But my long jaunts are usually a different kind of adventure that involves plenty of movement, fast-paced sightseeing and some awesome experiences packed into a short period of time. To call them “vacations” is a bit of a stretch since they aren’t always relaxing! 😬

If you crave fast-paced travel and a rich mixture of cultures and experiences, read on. In this post we’ll explore several different ways to book multi destination flights, talk about the pros and cons of each tool and look at some helpful example itineraries. Let’s go! ✈️

What are multi destination flights?

First things first, let’s define our terms. Sometimes multi destination flights refer to a special kind of ticket called a round the world (RTW) ticket. Personally I book my multi destination flights as separate legs and have never used an RTW ticket – but we will take a look at both approaches since some travelers rave about the convenience of RTW travel.

Round-the-world tickets

Even the most seasoned travelers are puzzled from time to time by airline pricing and schedules. Why do flight prices vary so dramatically from day to day? Why is it a thing to have layovers in cities that aren’t en route to your final destination? And – side tangent – why are flights between US cities ridiculously spendy even though the cities aren’t THAT far from each other?!

While you can save money by booking individual flights you’ll have to do research to make sure you’re choosing the best days to travel and selecting the most efficient routes. If you’re more concerned with speed and convenience and aren’t worried about your budget or flexibility, an RTW ticket might be your best option.

RTW tickets are usually offered by airline alliances. Airline alliances are associations of airlines that provide a network of different routes and share benefit programs. If you’ve spent any time at an airport it’s likely that you’ve seen these logos kicking around on airport lounges and aircraft paint jobs.

Major alliances offer passes (essentially another name for RTW tickets) that allow for travel on any airline within that alliance. The pass options depend on how many stops you want to take and the number of miles you’re planning to travel. For example, the low-end pass option might look like 26,000 miles of travel with a maximum of 5 “stopovers” – a stopover is defined as a 24-hour stop in any destination. On the high end, you could travel nearly 40,000 miles with 15 stopovers.

RTW passes often have these basic restrictions:

  • You have to end your trip in the same country where you began – the city of departure vs arrival usually doesn’t matter
  • Your ticket is valid for one year from the time that you take your first flight
  • You can only travel in one direction around the globe (i.e., you couldn’t backtrack from Asia to Africa or South America – instead you’d need to travel from South America to Africa to Asia in that order).
  • You’re allowed to change dates and times of flights on an RTW ticket, but you can’t change your destinations once they’re set

What are the pros and cons of RTW tickets?

In some ways, RTW tickets are pretty awesome. You pay an all-inclusive rate, have a plan in place from the very beginning and don’t have to worry about stringing together an itinerary along the way. They can also be affordable – a basic RTW ticket could cost you less than $2000 USD.

If you want the flexibility to change plans at the last minute, love scoring flight deals and don’t mind flying on budget airlines, you might want to book your multi destination flights separately – but we’ll talk more about that later. 

How do I book RTW tickets?

You have two main options for buying RTW passes. The first is to book directly online with an alliance.

Alliance Bookings

On the Star Alliance website the itinerary planning tool is intuitive and simple – I put together a sample itinerary just for fun. I like how they provide you with an estimated total and they make it impossible to break the “round the world” rule by only bringing up destinations that are beyond your origin point.


The tool on the OneWorld alliance site is pretty similar, but it prompted me to choose my flights before giving a price estimate.


After setting up the itinerary, you can choose your flights between each destination.

It took a moment for my options to pop up – I waited with bated breath – but once they did I had plenty of routes to choose from. I like the “via city” column since it quickly points out the layovers on each leg.

Easy peasy!

The last major alliance is SkyTeam. Interestingly, it’s the only booking tool that gave me the option to specify I’d be traveling with an infant. I’m not sure if that would have popped up later on with the Star Alliance or OneWorld bookings, or if I would have had to call in to add an infant to each of my flights (hopefully not…that sounds like an hours-long phone call!)

The SkyTeam tool also gave me the option to auto-generate a route or to handpick my stops.

I opted for the “choose your own route” option for consistency.


In conclusion, all of the alliance tools are super simple to use for anyone who has booked flights online. I can’t speak to the simplicity of traveling with the pass since I haven’t done it. If you’ve traveled on an RTW ticket (and think I should give it a shot), let me know in the comments!

Third Party RTW Companies

Remember how I said that there are two main options for booking RTW flights? If you want to buy an RTW ticket be sure to get quotes from third party RTW companies like AirTreks or STA Travel. I haven’t flown with either – but I had travel insurance through STA at one point (and was satisfied with it) and lots of travelers have good things to say about AirTreks.

I set up a simple itinerary on AirTreks to get a feel for their platform. For this example I decided to use one of my past itineraries so that I could compare pricing between booking with AirTreks and booking on my own. This isn’t the best “RTW” itinerary to use since it doesn’t venture beyond the US and Europe, but it does include multiple stops.

Their platform is pretty straightforward. Best of all, you aren’t hemmed in by limitations like traveling in one direction or hitting a certain number of stops/miles. Third party platforms have more flexibility to book across alliances and to use budget airlines – which can save you lots of $$$ at the end of the day.

After creating my trip I hit the “get your price” button…and waited. It took AirTreks more than a week to get back to me with pricing, but I was satisfied with the end result. The overall cost didn’t seem outrageous given that I was booking multiple flights and going through a third party agency.


I’d be curious to see what AirTrek’s pricing is like on a more elaborate itinerary that covers more ground since flights between European countries tend to be pretty cheap. Overall, I’d be happy to pay this amount for everything that’s included.

Next I checked out STA. I got a little lost on STA’s site because I delved into their pre-packaged itineraries (it doesn’t take much for me to go down the travel rabbit hole 🙈) These aren’t tours; just pre-made RTW routes that you can purchase for a flat fee. The Bobby Dazzler route looks pretty epic.


As far as I can tell, STA doesn’t have an online tool where you pick your route – you have to reach out to one of their travel experts to arrange for that. But one perk that STA has over other providers is that they have student discounts and flexible pay programs. With student life possibly looming on the horizon for me (again), I’m all about savings!

There are other third parties out there that offer similar RTW services and you can always reach out to a travel agent for flight planning, too. Truthfully I’ve never used a travel agent, but I’ve done other things that I “never” thought I’d do as a budget traveler, like pay for spendy tours and go on all-inclusive cruises. Sometimes it’s best to leave the planning to the experts and just enjoy yourself!

Planning Multi Destination Flights Without an RTW Ticket

You’ve stuck with me for awhile, and now you’ve got some great resources at your disposal for finding and booking RTW tickets. Again feel free to let me know in the comments if you’ve tested out any of the options I mentioned above – if so, I’d love to know how it went. Now I’m going to talk about the tools I consistently use to find and book multi destination flights on a budget.

credit @wistomsin | Unsplash


Skyscanner is my absolute fave (and no, they’re not paying me to say that – no one mentioned here is paying me anything, at least not at the moment, haha). For the last two or so years we’ve booked almost all of our flights through their site. It’s an aggregator similar to Kayak, Hipmunk, Expedia and the zillions of other third-party booking sites dotting the web. If memory serves I used Skyscanner initially because I liked their calendar view, which allows you to see various flight prices throughout a given month. Since budget is always top of mind when I travel, this feature has come in handy for me quite a few times.

If you’re really trying to save your stacks, you can use the “cheapest month” feature during your search. According to Skyscanner’s secret sauce, tickets to Hawaii are cheapest in April.

Skyscanner also has a multi city search feature. It’d seem natural to use that function to book multi destination flights, but I haven’t actually tried that yet since I like to 1) come up with my itinerary as I go and 2) book all my flights separately. If you have an itinerary in mind from the start it might be a good option to try this out, but you may run into an issue like this:

There are obviously individual flights available between these destinations, but Skyscanner couldn’t figure out the route as a whole. Sad face.

The All-Powerful “Everywhere” Feature

I’ve got to take a minor detour here to explain something about myself. If you know anything about me, you probably know that I love visiting multiple countries when I go abroad. It makes sense to me to hit up several countries in a region since I’ve traveled so far to get to that region in the first place…and it especially makes sense when I’ve endured a long flight with a toddler! It’s not everyone’s style of travel, but it suits my personality well and allows me to see lots of interesting things in just a few short weeks.

You also might know that I’m extremely budget conscious – if I set a budget for a trip, I almost always hit it on the nose. With those things in mind, I like Skyscanner’s “everywhere” search feature since it allows me to plot out routes that include multiple countries without blowing too much cash.

When I book multi destination flights I often start with a country or city in mind. We’ll begin with Salt Lake City since that’s my hometown (best hometown ever!) Once I have a jumping off point I’ll look at flights to “everywhere” to determine where I’d like to go next.

Turks and Caicos sounds pretty nice right about now. That probably has to do with the fact that my house is surrounded by over a foot of snow at the moment. Tickets are also pretty affordable at just $150! If you click on the down arrow you can see more details about the flights, included the fastest/cheapest ways to get to your destination.

It goes without saying that the fastest options with fewer layovers almost always cost more. However, some things still baffle me, like a flight to the exact same destination costing more despite having additional layovers. I’d take the $151 option any day over the $244 one!

Taking it to the next level

On international trips I always aim to see extra countries without compromising my budget. If I decided to take this trip to the dreamy tropical paradise of Turks and Caicos, I’d start looking for other nearby countries to tack on to my itinerary. I’d use the “everywhere” feature again to find my subsequent multi destination flights.

Let’s see where we can go from Turks and Caicos…

Depending on how much time and money you’ve got, you could easily piece together a 5-10 country Caribbean getaway with all these options. When I book my multi destination flights I always keep these considerations in mind:

  • Length and direction of travel between two given destinations – figure out where each place is relative to your other options and set up your itinerary logically. For example, if I wanted to visit Mexico on this trip and end where I started in the US, I’d begin the trip in the Caribbean and travel to Mexico toward the end. It seems like a simple thing but it’s easy to forget with so many options!
  • Getting home – let’s pretend that you start your trip in Turks and Caicos, jet over to the Bahamas and end in Costa Rica. Don’t forget to check the cost and availability of flights between your final destination and home. Oftentimes you’ll have tons of options, but it can vary if you’re hopping off the beaten path. For example, I’m putting together an awesome Spring 2020 South Pacific trip, and while flights are plentiful between New Zealand and the United States, there aren’t as many routes between the Cook Islands and the US. I’ve got to plan carefully to make sure we can get home without enduring a miserably long flight with tons of stops and a hefty price tag.

Other Tools for Finding Multi Destination Flights

I’ve waxed poetic about Skyscanner but by no means is it the only search tool out there. Heck, it might not even be the best – it’s just the one I’m accustomed to using. Let’s briefly look at some of the other aggregators that are helpful for finding multi destination flights.

Google Flights

Google Flights has a near-perfect setup for planning multi country trips. Type in your origin city and leave the destination blank; you’ll get tons of options. And it displays the info that matters most to the budget-savvy backpacker – the price!

Since the search tool is powered by the data giant Google, you can get interesting insights about the flight prices and best times to travel.


Like Skyscanner and Google Flights, Kayak makes it simple to plan multi destination flights by showing hundreds of options on its map search. I also like how they have categories for different styles of travel (in case you’re torn between the prospect of a steamy, romantic getaway or a lazy, sun-filled beachside escape). 

I haven’t used Kayak to book flights but they always seem to have the best deals on rental cars, so you’re likely to find solid airplane ticket prices on their platform as well. 


Hipmunk takes me back to the good ol’ days – I used their site to book some of the first flights I ever took as a college-aged backpacker. I’ve always liked their interface since it’s clean and easy to navigate. 

Simple, streamlined and easy to use – that’s about all you need when booking multi destination flights!

I’ve just scratched the surface here with my high-level view of flight aggregators. There are tons to choose from and most of them have search functions that are helpful for planning multi country trips. 

To sum it all up…

If you’ve made it this far, chances are that you love travel and want to see as much of the world as you possibly can.  Even neighboring nations have little subtleties and quirks that make them unique and exciting, which is why I try to venture beyond the typical tourist favorites.

Travel can be merciless money pit that sucks up every bonus check and claims every vacation day. It’s easily one of my most expensive hobbies (and that’s saying A LOT since I have some pricey pastimes! 🐎) However, you can easily maximize your time and money by finding affordable multi destination flights that allow you to see and do more each time that you travel abroad. And that’s not even accounting for travel hacking and a slew of other tips and tricks you can get flights for free – I’ll be sure to cover that in a future post!

Did I forget to mention anything important about multi destination flights? If so, please let me know in the comments!

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