Quick question: when you search flights, do you always check the round-trip box first? Most people do. It's the default. It feels like the safer, cheaper choice.
Here's the thing — it's not always true.
A friend of ours found this out the hard way a couple of years back, booking a trip to Portugal. Round-trip out of Newark was hovering around $940. On a whim, he priced out two separate one-way tickets instead. $610. He refreshed the page three times because he was sure he’d made an error somewhere.
He hadn't.
Turns out, flight pricing is a lot messier than "round trip = discount." A big chunk of it comes down to when you actually book — something worth sorting out before you even open a booking site.
The short answer? It depends — on where you're flying, when you're flying, and whether you're paying with cash or points.
- • Flying domestically in the US? Two one-ways usually cost about the same as round-trip.
- • Flying internationally? Round-trip is often a lot cheaper.
- • Booking with points and miles? Two one-ways are frequently the smarter play.
- • Landing in one city and leaving from another? Look into an open-jaw ticket before booking two separate flights.



