Yes, you can: 8 tips for strategically booking your first stopover

When you search for airfare from your home airport to your destination airport, you're getting an inflated price. Search engines just show you whatever predetermined fares the airlines have decided it costs to get you there, along with connections that are often either rushed and hectic or long and boring in places you're not interested in going.

I book one-way flights almost exclusively. One great reason is to build fun stopovers into your route. It can give you the opportunity to turn one vacation into many -- while saving several hundred dollars in airfare. There's a science to it.

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I'll show you the tools that make it easy for you to sniff out a cheap route to your destination while adding exciting stopovers.

What is a stopover?

When most people plan for a trip, they're only focused on point A and point B. Any extra stops in between are a hassle. Here are some helpful definitions of what happens to you on the way to your vacation:

• Connection: Any point during your journey when you have to stop at an airport that isn't your origin or destination. If your flight isn't nonstop, you've got a connection. Common parlance implies that these are normal, unremarkable stops (not hours and hours long).
• Layover: This definition is more rigid. For domestic flights, a layover is a connection lasting less than four hours. If you're flying internationally, a layover is any connection less than 24 hours.
• Stopover: If flying domestically, a stopover is any connection lasting more than four hours. If flying internationally, a stopover is any connection lasting more than 24 hours

Stopovers can either be really, really inconvenient (spending an extended period of time wandering the airport corridors), or very enriching (leaving the airport for some tourism in a city other than your destination). The latter is what this post is about.

When you build a stopover into your travels, you can make them for as long as you want (months, even!). It's a fun way to turn a boring commute into a hopscotch of bucket-list items -- and if you know the strategy, you can do it while paying far less for airfare than had you gone straight to your final destination.

Example: Building stopovers to Europe

As our example, I'll search from my home airport of Cincinnati to the island of Malta. The lowest price I can find is in early October for $952 round-trip. As you can see from the below screenshot, that's quite low. Google even claims the price is $1,240 cheaper than usual (that seems a bit steep). No matter, we can handily beat this price -- and throw in three or more fun stopovers while we're at it.

Google Flights has this really cool map search function that allows you to enter an origin airport but not a destination. If you're unfamiliar with Google Flights, read our Google Flights guide to become an instant expert. Just as a refresher, here's how it works:

1. Input your home airport
2. Leave the destination blank and click "Search"
3. Make your dates flexible by clicking "Trip in the next 6 months"
4. See the cheapest destinations around the world from your home airport

With this tool, you can basically mine cheap routes from any city. Once you figure out the notably inexpensive routes, you'll just have to play with dates to find the best prices. Let's walk through it.

Related: Guide to Google Flights

Step 1. Search hubs from your home airport

Note that this entire post will be a series of one-way searches.

Enter your home airport to see cheap routes from your origin. My home airport is Cincinnati. I simply leave the destination blank, search with flexible dates, and then slide that price filter (left side of the page) as low as it will go to search flights costing $50 and under.

My results are below. These flights will almost certainly be nonstop. I've highlighted hub airports I wouldn't mind having as a stopover: New York, Miami, San Francisco and Washington, DC. I'll keep these four airports in mind as I'll need them in step 3.

Step 2. Search hubs from your destination airport

I'm now repeating step 1 except I'm searching from my destination (Malta) instead of my home airport. I'm looking to see which cities offer cheap service to Malta. There are plenty -- most of Europe is super cheap once you get to the continent. I've again noted some fun options that I'd enjoy as a stopover, like Edinburgh, Vienna, Porto and Rome.

Step 3. Search routes between your stopover-worthy cities

Another fun feature of Google Flights is that you can search up to five origin airports at once. I'll now enter my choice stopover destinations from step 1 (Miami, New York, Chicago) into Google Flights, but again keep the destination blank. I'll then swing the map over to Europe to see any potential cheap transatlantic routes. I put the price filter at $300 or under, as that's all I'm willing to pay.

This instantly gives me hundreds of permutations between all airports in Europe. Now all I have to do is cross-reference the cheapest European airports with the airports that fly to Malta and then choose the one I want to visit the most.

As you can see, the cheapest flight to Europe is to Porto, Portugal. Clicking on the city reveals that the flight originates in Newark. For $167, I'll gladly make a stop in Portugal, the magical land of castles, wine and cobblestone streets.

Step 4. Enter your route into the Google Flights multi-city tool

The above steps have led me to the following itinerary:

• Cincinnati to Newark
• Newark to Porto
• Porto to Malta

I know it's possible to score a deal on all these routes. I'll pull up Google Flights again, and input these airports into the multi-city tool. Dates don't matter yet.

Step 5. Check the dates for each leg separately

The next step is to check all three legs separately to find a cheap date for each. This may be the most time-intensive portion of your research, though I don't find it to be a burden (it's actually fun). Just open a separate tab for each leg and pull up Google Flights to do your pricing.

My first leg is Cincinnati to New York. I've highlighted the cheapest dates in yellow. After I find the cheap fare I want, I'll look at the flights from New York to Portugal and Portugal to Malta. I'll tinker with the dates until the prices are low across the board and the time spent at each stopover is to my liking.

Step 6. Plug the cheap dates into your multi-city itinerary

Once you find your dates, head back over to your tab with the multi-city search and begin plugging in your dates. From Cincinnati to New York, I chose October 4. It's the cheapest date at $69 one-way.

Step 7. Book your ticket

After you've figured out how long you'd like to stay at each destination (along with low prices), you can view your final ticket price and book! The below one-way route from Cincinnati to Malta costs $260 (before any baggage fees). That's about $400 cheaper than simply searching for a one-way flight from Cincinnati to Malta.

Step 8. Use the same process to get home

You can use this exact same strategy for your return flight as well -- though it would be understandable if you tried to find the most direct route home after all that traveling.

After spending a few days in Malta, I built-in a four-day stopover in Paris, which set me up for a super cheap transatlantic flight back to New York. I tried to keep that connection as small as possible, as I'd already had a stopover in New York on my outbound journey. New York was just a necessary evil to cross the ocean for cheap.

Total cost for a round-trip?

The total cost of this ticket is $629 (plus potential bag fees, depending on the airline). That's $323 cheaper than that fare to Malta we looked at earlier -- a 34% savings! And if you're traveling with a friend or family member, you'd collectively save nearly $650. Plus, you get free visits to:

• New York
• Portugal
• Paris

For the same price, I could have strategically tossed in a few more destinations like Las Vegas, Italy, Lanzarote and London. That's even further removed from reality for the average traveler, though. Trying to keep it plausible over here.

Other tips

Beware of booking flights too close together

Yes, booking your own routes can save several hundred dollars over allowing the airline to work it out for you. But you're destined to spend a lot of money at your stopover cities.

If you're purely trying to save money on the way to your destination (i.e. not interested in side-trips), you'll have to schedule each leg closely together. The biggest caveat here is that if one flight is delayed for some reason, you could miss a series of future flights. Remember, you'll have to re-check your bags and go back through airport security for each flight.

Related: Best credit cards with trip delay reimbursement in 2021

Build time for complications into your itinerary. And be sure to use a credit card with travel insurance to buy your flights in case of trip delays or cancellations.

Search by city, not by airport

Google Flights allows you to enter city names instead of just airports. By entering the city, you'll find discounts you otherwise wouldn't have if you'd just typed in the airport code. For example, instead of typing in CDG for flights to Paris, you can just type "Paris," and Google Flights will search for routes that include other airports that serve the Paris area:

• CGD
• ORY
• BVA
• XCR

Some of these airports specialize in low-cost carriers, so you'll often see lower fares that don't fly to Charles de Gaulle, the main airport serving Paris.

The same goes for any city served by multiple airports. Type New York instead of JFK, San Francisco instead of SFO, London instead of LHR, etc.

Use miles and points for the outbound or return

Hopping around is fun -- for a while. But if you've built a load of stopovers into your outbound journey, you may just want to get home without any extra hassle. In that case, use miles to book a flight home from whatever obscure airport you're at to whatever obscure airport you're from.

For example, a flight from Malta to Cincinnati (generally) costs 30,000 American Airlines miles and ~$110 in taxes and fees. Yeah, that means you'll only save $257 over the return itinerary we pieced together -- and you won't get a stopover in Paris -- but it's effortless, and there's nothing to think about. American will carry your travel-weary cadaver all the way back to your bed at home.

Related: How to book your first award flight

How to avoid the worst low-cost airlines

Some of these fares are ridiculously cheap. Like, fly across Europe for $12 cheap. The problem is that some airlines often nickel-and-dime you; sometimes it feels like they go out of their way to make your trip miserable, whether it's charging to use the bathroom, lambasting you with advertisements or meticulously designing seats for optimum discomfort.

If flying Ryanair is out of the question for you, narrow your search by clicking the "Airlines" tab at the top of the Google Flights search map and checking all the alliances. Most low-cost carriers aren't part of an alliance.

Skyscanner is a good supplementary tool

Similar to Google Flights, Skyscanner allows you to search for flights to anywhere, as well. It's a little more functional than Google's tool in a couple of ways:

• You can search for flights to everywhere nearly a year into the future with Skyscanner. Google Flights only allows for flexible dates up to six months in advance
• Your origin can be broad with Skyscanner. For example, you can type in "United States," whereas Google requires an actual origin airport

This can be a good tool for finding the long legs of your journey. If you enter the U.S. as the origin and Europe as the destination and then select the "Cheapest month," it'll give you a very digestible list of European destinations, sorted by price. Click on the destination to see the specific route.

Related: Best flight booking apps

Bottom line

You can easily save hundreds of dollars by locating a series of cheap one-way flights to reach your destination -- and swing by a few other enchanting locations while you're at it. Be sure to book your flights with a travel credit card like the Chase Sapphire Preferred® Card, which covers you in case your flights are canceled or delayed. It's also got a 60,000-point bonus after spending $4,000 within the first three months of account opening. That's worth $1,6200 in travel, per TPG valuations (and a ton more if you know how to redeem Chase Ultimate Rewards for maximum value).

Let me know if you've got a better way to build stopovers into your travels! And subscribe to our newsletter for more practical money-saving travel tactics.