Why would you book a stopover on a one-way trip?

On Wednesday I saw this post by The Miles Professor explaining how to book stopovers on one-way Alaska Airlines award tickets.

The thing is, it's not immediately obvious why you would ever do this.

As The Miles Professor writes:

"One of my favorite ways to use stopovers is to schedule a stopover in my actual home city and use the stopover to connect two completely different trips."

Of course Alaska Airlines has a zone-based, not distance-based, award chart, so there's no reason you would need to book two round-trip tickets from your home city as two one-way trips with stopovers in your home city. For example, a Seattle resident could book the following two one-way tickets:

  • LAX-SEA (stopover)-BOS
  • BOS-SEA (stopover)-LAX

Each of those tickets would cost 12,500 Alaska Mileage Plan miles, assuming there's low-level award availability. But remember, our hypothetical passenger is a resident of Seattle, so they'd need to find some way to get to LAX in the first place, and some way back from LAX at the end! Each of those one-ways would also cost 12,500, bringing the total cost for 2 roundtrips to 50,000, just as it's supposed to be.

Now, at this point you've probably seen the sleight of hand I'm pulling; in fact our passenger knows better than to spend 12,500 valuable Alaska miles on a short West Coast hop, and instead transfers 7,500 Chase Ultimate Rewards, Starwood Preferred Guest, or American Express Membership Rewards points to British Airways Avios, and ends up with reservations that look like this:

  • SEA-LAX – 7,500 Avios
  • LAX-SEA (stopover)-BOS – 12,500 Mileage Plan
  • BOS-SEA (stopover)-LAX – 12,500 Mileage Plan

Here we've booked two-and-a-half round-trips for the price of one-and-a-half roundtrips. Not bad! Of course our passenger still has to find a way back from LAX if they decide to fly that leg, but even if they don't, they still end up a one-way flight ahead of the game, which isn't nothing.

If that's the obvious use for stopovers on one-way trips, I thought it'd be interesting to see which others I could come up with.

4 reasons to book stopovers on one-way award tickets

  1. See more cities. As you can see in the comments to The Miles Professor's post, you can also book stopovers on one-way Alaska Airlines partner awards, so if you're booking an award ticket on a partner airline like KLM, you can stop over for a few days and enjoy Amsterdam on your way.
  2. Cheap awards to Hawaii and Mexico. Since you can book award tickets from anywhere in the continental United States to Hawaii and Mexico for the same price, which is less than twice the cost of domestic awards, you can book future, onward travel to Hawaii for just 7,500 miles or Mexico for 5,000 miles, compared to the 20,000 and 17,500 Mileage Plan miles, respectively, you'd have to pay to book a separate itinerary.
  3. Position for future flights. I showed one example of this technique above, but you can also use it to position for flights on other carriers. For example, United operates an international hub out of San Francisco, but you might have difficulty finding low-level award space between Seattle and San Francisco on United-operated flights. Instead, you can use your free one-way flight to position to San Francisco on an Alaska Airlines-operated flight.
  4. Because you can. As long as you book your speculative onward connection at the end of your itinerary, you may as well tag an extra leg onto your reservation. Who knows, you might even end up using it! Just don't book a speculative connection at the beginning, since a missed first leg will typically cancel your entire itinerary.


Free one-ways are a fun and easy way to take advantage of airlines' generous award routing rules.

Which reasons to book a stopover on award tickets did I leave out?

Free one-ways on American award reservations

We've already discussed the basics of adding a free one-way flight before or after a round-trip award reservation on Delta and on United.  Free one-ways on American Airlines are a little trickier than on either of the other traditional carriers.  As always, in order to book a free one-way flight, you need to use a stopover.  However, American only allows stopovers on award tickets at the "North American gateway city," which is the airport where you depart or arrive North America.  This post has a list of which cities are considered North American gateway cities with different American partners.

Therefore, the only way to add a free one-way to the beginning or end of your itinerary is if you live in your North American gateway city, or can get there cheaply or easily.  For example, if you live in Boston, then as long as you depart or arrive North America on a flight from or to Boston, you can add an earlier or later one-way flight at the beginning or end of your reservation.  Below is a simple example.  On the outbound international leg, Boston to London, Boston is the North American gateway city.  That means that I was able to add an unrelated, free one-way flight from Dallas to Boston at the beginning of the itinerary for the same miles as just the international round-trip:

On the return flight I found, Chicago is the North American gateway city, so it would be possible to stopover there if I hadn't used the stopover already at the beginning of the itinerary.  Of course in order to get from Boston to Dallas in the first place you'll need a paid one-way ticket or an award from an airline that allows one-way awards at half the price of a round trip, like United or American.

Free one-ways on United award reservations

Round-trip United award reservations allow 2 open jaws and 1 stopover.  As we saw when booking free one-ways on round-trip Delta award reservations, we need to use one stopover and one open jaw to book a free one-way: the stopover in our origin city, then the open jaw to the destination of our free one-way flight.  You can use the other open jaw however you like.

Fortunately, United's booking engine actually works, unlike Delta's, so you can price out and book a free one-way ticket simply and easily online.  Here's a sample search for Chicago (a United hub) to Frankfurt (a Lufthansa hub), plus a free one-way flight to San Francisco at the end:

Notice that our later trip to San Francisco has nothing to do with the original roundtrip itinerary to Frankfurt.  It's a month later.  But sure enough, this prices out in Business Class just like a roundtrip without the one-way flight to San Francisco: 100,000 miles plus taxes and fees.

Free one-ways on Delta award reservations

One of the least appreciated aspects of award reservations is something discussed in chapter 4 of the book: free one-way flights at the beginning or end of award reservations, which are possible because of the flexibility of some airlines' routing rules. Today I'll take a closer look at just how to take advantage of free one-way flights on international Delta award reservations.

First, we'll put together a basic award reservation: Detroit to Amsterdam in Economy class.  We'll follow the steps I describe in chapter 4, which you can read more about here.

Step 1: Find outbound availability.  Here's a non-stop flight in Economy at the "low" 60,000 mile level from Detroit to Amsterdam:

Step 2: Find return availability.  Here's a flight back from Amsterdam to Detroit a few days later:

Since both these legs are at the "low" level, we know we can book this itinerary for 60,000 Skymiles plus taxes and fees.  Even if it can't be booked online, you can call into the reservation center and they'll be able to find each leg, although they may charge you a telephone reservation fee unless you're a Platinum Medallion or higher.  In this case it turns out we can book the reservation online:

Now let's see about our free one-way flight.  So far we've put together a great low-level award reservation in April.  Now suppose you have some family in Portland and every August you get together there to watch Star Trek in the Park.  Understandably, you'd like to get there as cheaply as possible.  What about a free one-way flight?

Step 3: Find a low-level flight to your next destination.  Here's a low-level flight to Portland in August:

Step 4: Use the Multi-City search to put your final reservation together:

Step 5: Select your flights, and make sure the reservation prices out correctly.  In this case, there was no problem at all.  Note that the entire reservation, with the one-way flight to Portland, costs the same number of Skymiles as the original round-trip from Detroit to Amsterdam.  You'll just pay an extra $5 in boarding fees:

And that's the simplest version of a free one-way flight on a Delta award reservation!  There are just a few more things to keep in mind:

  • The free one-way can be at the beginning OR end of the award reservation.  In the above example we put our trip to Portland at the end of our trip.  Alternatively, we could get a free one-way FROM Portland to Detroit at the beginning of the award reservation.  In either case our trip has to pass THROUGH Detroit: it would be an invalid routing to book a flight from Detroit to Portland and THEN from Detroit to Amsterdam on the same reservation.
  • Use of this trick is somewhat limited by what's known as the "Maximum Permitted Mileage" between two cities.  In this case, our trip from Detroit to Portland fit under the Maximum Permitted Mileage for an itinerary from Detroit to Amsterdam, but a flight to Hawaii might not have.  You can read more about Maximum Permitted Mileage and other restrictions on free one-ways over at the Points Guy's blog or in this post at MileValue, who discusses free one-ways on purely domestic reservations.