One way or round trip?

Good morning, travel nerds, and welcome back to Daily Drop, the newsletter that solves all of life’s great mysteries (as long as they involve travel).

Speaking of life’s great mysteries, let’s tackle one of the most common questions in travel, shall we?

• 🤔 One way or round trip?

• 💳 Current Transfer Bonuses

🤔 Should you book one way or round-trip?

Today, we’re answering a question I get all the time:

And like most things in life (and travel), the answer is: it depends. 🤷🏼‍♂️

I’m going to break down the pros, cons, and real-life examples so you can make smarter bookings — and maybe save a ton of money or points in the process.

(Also, full disclosure: I personally almost always book one-ways… but I’ll explain why that might not always be the best move.)

✈️ The Case for Round-Trip Bookings

As many of you know, airlines sometimes heavily discount round-trip fares compared to booking two one-ways, making round trips great for simple trips where you know your dates.

Generally speaking, this is true of international booking on full-service carriers like this British Airways example, where the one-way flight is more than double the cost of the same flight… plus a return leg:

But lately, we’ve been seeing this happen more and more often with domestic flights, too - including some tasty fares right at home in the U.S.

For example, check out this one-way flight from Nashville to New York in June:

Now look at that same exact flight but with a return leg to Nashville four days later:

As you can see, you’re saving $149 by doubling the amount of flying.

While this is less common, it’s always worth looking at the prices before weighing the other pros and cons of booking one way versus round-trip.

😞 Downsides to Round-Trip:

The main downside to booking a round trip is that the airline’s policies apply to the overall booking.

If you need to make a change before or during your trip, your plans change, or you want to cancel one part of the trip, you might run into some issues.

Furthermore, sometimes award tickets don’t price favorably as round trips (more on that below).

😍 Why I Love Booking One-Ways

There are three main reasons that I always opt for one-way tickets:

1. Flexibility

2. Flexibility

3. Flexibility

I’ll give you a sec to take notes if you need to.

But seriously, booking one-way flights makes it MUCH easier to pivot plans if life changes. (And my life changes… a lot.)

There are some other pros to booking one-ways:

• Sometimes cheaper when using points or positioning flights.

• Airlines (especially low-cost carriers) often price one ways fairly.

• You can mix airlines, alliances, or cabins to optimize value.

For example, if you’re planning a trip to Europe, you might find an amazing flight on a budget airline to get you there, like this flight from New York (JFK) to London (LGW) for $125:

But maybe on the way back, there isn’t a similarly cheap flight that lines up with your plans. Or maybe you’re flying back from a different country.

Then, you can just book a different one-way flight with miles and points, like this awesome deal from Frankfurt (FRA) back to New York on Condor for 27,500 Alaska miles in economy or 70,000 in business class.

😬 When One-Ways Can Backfire:

Obviously, there are downsides to booking one-ways as well…

For me, these boil down to the following:

• If your trip is straightforward and your dates are locked down, you’ll be missing out on some savings by booking as one-ways rather than a round trip.

• One-ways give you more things to manage. If something goes wrong with one of the flights, a ticket booked on a different airline with a different program won’t be on the hook to help you change your plans and resolve any chain-reaction issues.

Finally, there are some award program considerations to be aware of…

For example, some programs, including Delta, offer discounted points rates when booking round-trip versus one-ways.

This flight from Atlanta to London next month costs 38,000 Delta SkyMiles when flying one way:

But if you book a round-trip, you’ll pay a grand total of 40,000 Delta SkyMiles for the same exact flight AND a return flight.

In other words, you’re getting an entire extra trip back across the Atlantic for just 2,000 more miles.

🤔 So… What’s the Move?

Here is a simple summary of what we’ve covered:

• If it’s a simple trip with firm dates, always check round-trip pricing.

• If you need flexibility, booking one ways (especially with points) is often safer.

• For international cash fares, round trips can save hundreds of dollars.

• For award tickets, check program rules — some programs price per segment, others give discounts for round trips.

• Low-cost carriers: usually, one ways are fine and priced fairly.

• For complex trips with multiple stops or open jaws, one ways give you control.

Here’s the bottom line:

I book one-way trips because my schedule changes constantly, and I love building trips piece by piece. I think of booking travel as part of the travel experience — and one that I love.

But if you’re booking a standard trip — especially international — and the dates are locked in, round-trip fares could save you real money.

Whichever way you book, just don’t overthink it.

And if you do… I’ll be here to help talk you through it (or at least send memes to make you feel better). 🤗

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That’s all for today, folks. I hope today’s newsletter gave you some things to think about when it comes to booking flights for your next trip.

Before I let you go for the weekend, tell me:

Take care, stay healthy and happy, and have a wonderful weekend.

Love you all 😘

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