Photo: Oskar Kadaksoo | Unsplash
Here's When Buying Two One-Way Flights Is Cheaper Than a Round-Trip Ticket
Living in Nashville means my airport is not exactly an international hub. Finding affordable flights sometimes feels like I’m back in Algebra 2, trying to figure out what x equals and why that random letter is even there.
Recently, I searched for a cheaper ticket to Guatemala. I priced out one-way flights on three airlines, United, American Airlines, and Delta, mixing departure and return days and comparing total costs. It’s part art, part science, and unfortunately, part math. And it doesn’t always work. This time, it didn’t. American Airlines round trip won my personal airline March Madness.
Most travelers default to round-trip tickets because they’re easy and usually cheaper. But not always. There are specific scenarios where booking two one-ways saves money or gives you flexibility that a round trip simply can’t.
Here are the best times to book a one-way flight.
-Kelsey Wilking, newsletter editor
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D E A L S
Travel Offers Worth Booking
No affiliate links. Just solid finds.
Daily Drop round-trip flights:
Bahamas In A Day: Fly from Fort Lauderdale to Bimini and back in a single day for $550 when booked by March 1.
Celebrity Cruises: 75% off your second guest’s fare and up to $600 off per room. Ends tonight.
Disney Water Park Seasonal Pass: Only $89 plus tax, valid through May 9, 2026.
MIMARU Hotels, Japan: Pack less and rent clothes upon arrival at select properties. Available through March 2026.
G U I D E
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Photo: National Museum of African American History and Culture/AlanKarchmer
With 12 exhibitions, nearly 37,000 objects, and 183 videos, there’s no single right way to experience it. Curators even say seeing it all in one visit is nearly impossible. This focused one-day route helps you move thoughtfully through 600 years of powerful, essential history.
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Photo: Suzie Dundas
Hitting the sweet spot between office-ready and airport-practical, this backpack looks sharp in the conference room and performs on travel days.
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Photo: Ritz-Carlton New York, NoMad
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Travel Well
The Matador Editorial Team
*Here at Matador, we're always looking for the best travel deals. We may receive a commission via affiliate links in this newsletter. Prices and availability can change at any time.