Should You Ever Book Two One-Way Tickets Instead of a Round-Trip Flight?

Two one-way tickets can sometimes unlock cheaper fares and help travelers maximize points and miles—if you know when to use the strategy and how to avoid the risks.

A collage depicting two cutouts of airplanes flying in opposite directions that are placed atop a background with three llamas walking in the Patagonia region

When it comes to one-way flights versus round-trip fares, comparing flights never hurts.

Photos by Unsplash, design by Elizabeth See

Most of us don’t think twice when we start a flight search: The “round-trip” box is already checked, and it seems like the easiest option, with one booking, one confirmation, and ideally the best price. However, with today’s dynamic airline pricing in which fares shift constantly based on demand, competition, and timing, that assumption doesn’t always hold true. And because airlines often set prices for each leg of a trip individually, two one-way tickets can sometimes cost less than a round-trip fare.

Booking two one-ways can also widen the variety of flight times (meaning more options for both departures and returns) and give you better opportunities to maximize points and miles. Still, the strategy isn’t for everyone. Two one-way tickets may come with fewer loyalty perks, and they come with more risk, as you may have to cancel or reschedule your return flight if your outbound flight is canceled. Here’s what to know when contemplating two one-way tickets versus a round-trip booking.

When one-way tickets make sense

There are clear situations where booking two one-way tickets outshines a traditional round-trip ticket. Cost is one. Pairing two one-way flights to Europe and back can sometimes save travelers up to 35 percent when compared to round-trip flights across the pond, according to Jesse Neugarten, CEO of Dollar Flight Club, a subscription service that helps travelers find the best flight deals.

Open-jaw trips, in which you fly into one city and out of another, are another strong reason to book two one-ways. A positioning flight, which is a separate one-way flight booked to reach a departure city with cheaper fares, can also pay off if you allow plenty of buffer time. And, as mentioned above, if you really need or want certain departure and return times that are not offered by a single round-trip flight, you can split the journey into two one-way flights to have more options that suit your needs.

The strategy works even better with award travel. “When using points, it’s almost always better to book two one-ways,” explains Tiffany Funk, cofounder of Point.me, a rewards search that helps travelers find and book flights with their points. Because award fares are generally priced per segment, travelers can mix and match airlines without incurring extra costs.

Quinn English, who helps travelers maximize their personal and business points and miles through his company, FreeQuinnt Flyer, agrees. “Ninety-nine percent of the time, I book two one-ways. It’s a lot easier to piece together award flights this way, and it opens up a ton of options.”

The potential downsides of booking two one-way tickets

Booking two one-way flights instead of a round-trip isn’t usually too big a gamble, especially for leisure travelers with flexible schedules. “I don’t think there are really any risks with booking two one-way flights,” says English. Still, it pays to check prices carefully.

“Earlier this year, we heard of airlines testing inflated one-way [domestic] fares for single travelers,” notes Katy Nastro, travel expert at flight deal tracking site Going.com. “There was definitely outrage against this tactic, and largely, airlines backed down.”

The caveats come down to timing and disruptions. If your trip is tightly scheduled—say, flying out and back for a same-day meeting—a delayed or canceled outbound flight could leave you unable to make your return, leaving you with little to no recourse since the return flight was a separate booking, Quinn explains. If your one-ways are booked on different airlines and your first flight is canceled, the second airline isn’t required to help, and you may have to cancel the return flight or buy new flights altogether.

Loyalty programs can also complicate the equation for some. In an effort to keep customers within their ecosystem, “airlines prefer [that] you buy a round-trip [flight],” says Nastro. “But sometimes you need to be more loyal to cheap flights than one airline.” Neugarten echoes this, noting that for the average leisure traveler, saving 25 to 40 percent on airfare usually outweighs the value of a few extra miles earned.

Smart safeguards

Taking a few smart precautions can help prevent risks from escalating into major issues. To that end, Nastro recommends booking directly with the airline—whether over the phone, on their website, or through the app. On the latter, she notes that “airline apps have come a long way, and much of what you may need—like changing seats or flights—can now be done within them.”

For financial protection, Neugarten suggests booking with a credit card that offers strong trip coverage. “If a flight gets delayed or canceled, those benefits can make all the difference.” He also recommends travel insurance to cover cancellations, illness, or other curveballs, “which makes the savings from two one-way tickets a lot less stressful to lock in.”

The bottom line

With a bit of planning, two one-way tickets can unlock significant savings—so long as you’re willing to trade a little airline loyalty for greater value. At the very least, it’s worth comparing the flight options before you book.

Lauren Dana Ellman is a New York–based writer and editor whose work has been featured in Condé Nast Traveler, Travel + Leisure, ShermansTravel, Well + Good, Allure, and more.
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