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The Ultimate Guide to Travel Hacking: Maximizing One-Ways and Stopovers

Are you squeezing the most value from your airline miles by maximizing one-ways and stopovers to your benefit?

Do you know which airlines allow free or discounted one-ways and stopovers and how to book them?

In this guide, we’ll discuss one-ways, stopovers, and how to use them to your advantage. You’ll also find real examples to illustrate the info discussed. 

Ultimate Guide to Travel Hacking Maximizing One-Ways and Stopovers
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The Ultimate Guide to Travel Hacking: Maximizing One-Ways and Stopovers

There are different strategies for getting the most from your points and miles. Stopovers get the most attention because they allow you to add another destination to your itinerary typically for no extra miles. We’ll talk more about how to take advantage of them below.

But, let’s take a step back first. 

We all know the difference between one-way and round-trip flights. The majority of travelers default to booking round-trip flights mostly because round trip cash flights offer more value price-wise than one-way flight bookings.

However, the same logic doesn’t apply when using points and miles to book a flight.

One-way searching and booking can be an effective strategy for finding the award space you need and for saving valuable points and miles.

Benefits of Searching & Booking One-way Award Flights

Airline loyalty programs have been ditching their fixed award charts in favor of dynamic pricing models. This has made it harder to know if you’re getting the best price on your award ticket. 

It can also be hard to find saver award space, which is what you’re looking for to get the best award pricing. And believe it or not, round trip searching doesn’t always show all of the saver seats available.

The result is that you could end up paying more than you need.

Instead, search for available space in one-ways. You may be surprised to see flight options that didn’t appear in a round trip search. You may even find available space when a round trip search errored out.

Some airline websites return an error for your whole itinerary if there’s 1 segment without award seats even when there’s space on the other segment(s). 

This is where you need to be savvier than the airlines think you are. 😉

Try searching in one-ways to find the availability you need. Then, try to find the exact same flights on the exact same dates in a round trip search. This is the simplest scenario because, if you find what you need, you can then book the award itinerary online.

However, if the round trip search doesn’t show the one-ways you found, call the airline and feed the agent the saver flights you’d like to book to piece together the itinerary you want at the saver-level price.

If you have to call, keep in mind airlines typically charge a phone booking fee.

Explain to the agent you could not book this exact roundtrip online because only the standard award space was showing for a part of your itinerary. This should be enough for the agent to waive the online booking fee.

customer service agent

In addition to searching one-ways, booking one-ways can also be extremely worthwhile.

You can take advantage of different award programs and use different points and miles to book your departure and return flights. 

This is also a great way to use up mileage balances that are only enough to cover a one-way award flight.

It’s also perfect if you find availability with one airline for the departure and another airline for the return flight.

Booking one-way flights also allow you to open-jaw how you’d like without any restrictions imposed by award programs. (Open-jaws are when you fly into 1 airport but out of another airport.)

Lastly, one-way award flights allow you to choose from cheaper-priced dynamic awards. Not all dynamic pricing is calculated the same way. There’s quite a bit of variability. 

This makes it important to search, compare, and book the best-priced segments.

Maximizing with Free or Cheap One-Way A.K.A. a Stopover

Some airlines allow you to add stopovers on award itineraries. Adding stopovers to award tickets adds a ton of value to your redemption.

Stopovers on domestic itineraries are when you stop for more than 4 hours. International stopovers are stops of more than 24 hours.

United and Alaska Airlines allow free one-ways on award travel. (Yay!) American and Delta do not allow them. (Boo!)

Other airlines, like Aeroplan/Air Canada and ANA, allow stopovers, too.

This post uses examples of United’s Excursionist Perk and Alaska Airlines’ stopover policy to highlight some of what’s possible when you add stopovers to award itineraries.

DP United Airplane

Stopovers allow travelers to see another place typically for 0 extra miles.

Award programs that allow stopovers have their own rules. Some allow stopovers on one-ways. Others require a round trip award flight booking.

Consider the example below allowed by United’s Excursionist Perk.

An award traveler could fly from New York City to London. Stop in London to visit for a period of time before journeying onward to the final destination, Rome, for no additional miles.

When it’s time to return home, the traveler flies out of Rome back to New York City. 

This stopover itinerary costs the same number of miles as a basic round trip itinerary with no stopover.

Stopover Example Map
Credit: Great Circle Mapper

United’s Excursionist Perk allows stopovers for international destinations and when you fly from the 48 contiguous states to Hawaii. Free one-ways/stopovers cannot be booked if your itinerary stays within the mainland United States and Canada.

Stopovers can also be combined with open jaws. United allows 2 open jaws on round trip award itineraries.

Let’s add to the above itinerary.

Stopover Open Jaw Example Map
Credit: Great Circle Mapper

For this itinerary, we used United miles to book a round trip itinerary with 1 stopover/free one-way and 2 open jaws. The award begins by flying from New York City to London for a stopover of more than 24 hours.

During this time, you travel from London to Paris by train and enjoy Paris. When it’s time, we fly from Paris to Rome. While in Italy, make your way south to Sicily and eventually fly back to New York City.

This award itinerary would cost the same as a typical round trip…except you get several more destinations for 0 extra miles!

There are specific rules to know about using the Excursionist Perk to add stopovers to award flights. Find out all the specifics in this guide all about how to redeem United miles for the best value.

Airplane parked at the gate

Alaska Airlines is also quite generous with its stopover rules.

Alaska Airlines is a member of the Oneworld Alliance. And it also has non-alliance airline partners you can book flights on with your Alaska airline miles. 

Alaska’s partners include airlines like American Airlines, British Airways, Cathay Pacific, Emirates, Fiji Airways, Hainan Airlines, Japan Airlines, Icelandair, Korean Air, LATAM, Qantas, and Ravn Alaska.

Alaska Airlines has one of the most generous stopover policies on award tickets. You can have 1 free one-way on a one-way award ticket and 2 free one-ways on a round trip award ticket.

It’s not possible to use your free stopover on a one-way award ticket as your return home. But you can use the stopover to put together a lot of very valuable itineraries with great destinations.

You can use 1 partner airline per one-way award and of course, Alaska Airlines, to make use of free one-ways. For this reason, it rarely makes sense to book roundtrip Alaska award itineraries. By doing so, you box yourself into using just 1 partner for the entire award ticket.

Let’s look at an example of a free one-way with Alaska Airlines and its partners.

I searched on Alaska Airlines for a one-way from Seattle to New York City in October and a one-way from New York City to Dubai a week later.

Alaska Stopover Example

The above screenshot shows both flights for 42.5k total Alaska miles in economy and 82.5k miles in Business class. This is the total price for both segments because the free stopover is triggering for this itinerary.

Click on where it says “1 stop” to see the flight details.

Alaska Stopover Details

I’ve followed the rule of using only 1 partner, in this case, Emirates. Alaska Airlines will fly the Seattle to New York City leg of the itinerary. 

If I select economy class, the 42.5k Alaska Miles is how many miles I need, according to the Alaska partner award chart for Emirates, to fly from New York City to Dubai.

Alaska’s flight search did not add the 12.5k miles needed to fly from Seattle to New York City. This is my free one-way.

The 82.5k miles for business class is worth it. I’d fly from Seattle to Dubai entirely in business class. The New York to Dubai segment in business class sells for $5k on the same date.

If you run into an error message on Alaska’s website, it could be something to do with the stopover rules. However, it could also just be that 1 segment doesn’t have availability.

Search for each segment separately and then build your one-way itinerary with the stopover once you know the dates that have space. 

What other airlines allow stopovers on award tickets?

Not all airlines allow stopovers. But the ones that do can be an excellent way to redeem your points and miles.

Rules vary for each program but here’s a look at airlines that allow stopovers on award tickets.

  • Aeroplan/Air Canada
  • Alaska Airlines
  • All Nippon Airways (ANA)
  • Asiana
  • Cathay Pacific
  • Japan Airlines
  • Korean Air
  • Singapore Airlines
  • United Airlines

Booking strategies like using one-ways, open jaws, and stopovers can greatly increase the value you’re getting for your hard-earned points and miles.

Understanding the rules for airlines that allow stopovers on award tickets comes with a learning curve…but with so many possibilities and lots of upsides.

Are you finding it hard to redeem your points and miles?

Would you like to develop a step-by-step booking strategy and learn the ins and outs of must-know award programs including how to effectively add stopovers?

Join the waitlist for Booking Award Flights Made Easy and be the first to know when enrollment opens.

Booking Award Flights Mock Up

It’s a proven 6-module course that teaches award booking strategies so you can get the most from your points and miles without the frustration, overwhelm, and stress.

How have you maximized one-ways and stopovers with your points and miles?

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24 thoughts on “The Ultimate Guide to Travel Hacking: Maximizing One-Ways and Stopovers”

  1. I am intrigued, but also slightly confused. If JFK is your “home” airport, where you “stopover” until your trip to Dubai, how did you get to Seattle, and how are you getting home from Dubai? Are these booked as separate one-way (presumably award) tickets? Thanks for alerting us to the potential of this type of booking!

    1. Jackie Sills-Dellegrazie

      Hi Ann and thanks for your comment. I think the beauty of the Alaska Airlines free one-ways is that you are booking just that..one-ways which allow for a lot more flexibility. So for this itinerary to work I would have had to come from someplace else before arriving into Seattle. Maybe that’s JFK (with different miles or cash) or maybe someplace else. As for getting home from Dubai, I would have to book that. However, maybe Dubai is not my last stop. I could visit other places in the region or fly more cheaply to SE Asia. I can use Alaska miles to do a similar free-one-way ticket scenario to another destination and then home. I could also use other miles I have or even pay cash.

    2. Jackie Sills-Dellegrazie

      Do some experimenting with the airline websites. It’s amazing what’s possible.

  2. Wow, there’s a lot of info to digest here! I haven’t flown Alaska before, and wasn’t familiar with their Free One-Way program, good to know! I love taking advantage of stop overs and layovers to see other destinations. We had once spent the day exploring Sydney, Australia traveling from Chile to New Zealand, it was great!

    Thanks for sharing your research and great examples, I’m not even going to think of booking any future flights until referring to this again first 🙂

    1. Jackie Sills-Dellegrazie

      Thanks, Heather. 🙂 How great you got to spend the day in Sydney in between Chile and New Zealand! You just can’t help but feel like a jet-setter, right? Hope you’ll be able to make use of a free one-way with Alaska at some point. 🙂

    1. Jackie Sills-Dellegrazie

      Thanks, Claire. Yes, you definitely should! Start out basic, with just a stopover in the middle of your trip. With practice, you’ll be piecing together more complex itineraries.

  3. Wow, thats definitely a lot to know but like you said, practice! I haven’t tried this yet but I will definitely be trying this out and learn how to do this. Thanks for tips!

    1. Jackie Sills-Dellegrazie

      Thanks, Lieurene. That’s the key, practice. Experiment with the airline’s flight booking sites to see what is possible. It can take time but it’s so worth it when you squeeze tons of value from your miles. 🙂

    1. Jackie Sills-Dellegrazie

      Thanks, Jennifer. Yes, there are so many tricks to saving your miles. Stopovers and open-jaws do just that.

  4. Great tips, especially the bit about the stop overs! I am a bit obsessed with using miles for flights, so it’s always fun to read through articles like this! Piecing together segments/one way tickets can work so well sometimes, especially if you want to start and end in different cities!

    1. Jackie Sills-Dellegrazie

      Thanks, Jenna. I’m obsessed, too! 😉 It’s fascinating that airlines allow these types of bookings. It can be a great accomplishment to book a complex itinerary for few miles!

  5. Wow, great information and lots of “hidden secrets.” Had no idea that United was so generous in discounting miles needed for stop over. We have about 100K points on United that we are planning to use. Great tips…thanks for the tips and insights.

    1. Jackie Sills-Dellegrazie

      Hi Rosemary,
      Yes, United is super generous. Those 100k miles can really be a game changer if you use them correctly. Consider I flew to Chile roundtrip from NYC and then to Bangkok for only 80k. Remember to play around with United’s booking engine to experiment.

  6. These tips are real money savers! I have to admit that I really spend lot of time searching for the lights – it would be great to have some kidn of asssitant:) I will follow yoru routine and see if it works for me!

    1. Jackie Sills-Dellegrazie

      Thanks, Veronika. It can take some time to find the best flight and the best use of your miles. Have you checked out FlyerMiler? It can help you search for award flights by telling you which airlines fly where for how many miles.

  7. How I wish I live in the States just for this! Unfortunately in Malaysia, or in the surrounding regions, the best way to use airline miles is for an upgrade instead of for buying an economy class tickets – mostly because of the high surcharges that are imposed by the airlines in the region. I used to be able to pay just USD35 for a return flight between Dubai & Kuala Lumpur on Emirates after redeeming my air miles. Nowadays however, because of the surcharges, it’s more like USD200-USD250, which is about 30-50% of the promo airfares for the route, not worth the miles value when compared to upgrading…

    1. Jackie Sills-Dellegrazie

      Surcharges are a killer for sure. That’s too bad they’ve increased so much. Still, upgrades are better than nothing.

  8. Iceland Air lets you stay in Iceland for up to 7 days on your way to one of the other countries they fly to. I think more airlines should have incentives like this. Thanks for all of the great info!

  9. I need to read this again to truly wrap my head around it. It really sounds like something I need to take advantage of! Thanks for the pointing out this hack.

    1. Jackie Sills-Dellegrazie

      It’s true, Christina. You have to wrap your head around this. That’s why it’s good to play around with the airline websites to experiment.

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