Most travelers approach booking flights on a trip-by-trip basis. However, considering your travel plans as a whole presents opportunities to book more efficiently. If you’re accustomed to booking round-trip awards, a little creativity in your approach can lower your overall costs.
Air travel is conventionally framed as a round-trip itinerary with an outbound flight from origin to destination and a return flight in the opposite direction. This framing is intuitive because it aligns with the common travel experience of going somewhere and then coming home. Round-trip service to Orlando is a neat and natural fit for a trip to Disney World, and booking round-trip flights to Las Vegas or Phoenix makes sense when you’re visiting the Grand Canyon.
However, there are alternatives to this framing. Rather than thinking of flights as corresponding to a single trip, you can view them as a series of events that may stand alone or be connected to maximize convenience and minimize expense. One itinerary may involve flights pertaining to more than one “trip” in order to take advantage of cheap fares, preferred flights and advantageous routing rules.
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As a basic example, imagine you have plans to travel round-trip from Chicago to New York, Dallas and Seattle. Conventionally, these plans would be framed as three discrete round-trip itineraries starting and ending in Chicago:
Chicago – New York – Chicago.
Chicago – Dallas – Chicago.
Chicago – Seattle – Chicago.
You could just as easily frame these plans as a series of six one-way itineraries:
Chicago – New York.
New York – Chicago.
Chicago – Dallas.
Dallas – Chicago.
Chicago – Seattle.
Seattle – Chicago.
Alternatively, you could frame your plans as some combination of round-trip, one-way and multicity itineraries:
Chicago – New York (one-way).
New York – Chicago – Seattle (multicity).
Chicago – Dallas – Chicago (round-trip).
Seattle – Chicago (one-way).
No particular framing is inherently superior, but staying open to unconventional framings can help you save on award travel. The examples below will show you how.
Book one-way awards to optimize pricing in each direction
Many flights cost the same whether purchased as a single round-trip or two one-way itineraries, but booking separate one-ways has several advantages. You get more chances to lock in bargains as prices fluctuate, since you can book flight segments individually when they’re cheap and hold off when they’re expensive. That advantage compounds on awards that can be changed or canceled with no penalty, which allows you to rebook into less expensive itineraries as they become available.For example, this Alaska Airlines search shows round-trip itineraries from Seattle to Chicago on Oct. 9-21 starting at 37,500 Atmos Rewards points:
What the search doesn’t show is that the outbound portion of that itinerary starts at 27,500 points, whereas the return costs as little as 10,000 points. Instead of booking round-trip service from the start, you could book the return flight by itself and wait to see if prices drop before you book the outbound flight.
One-way awards also free you from the limitations of booking with a single carrier. You can fly with whichever airline offers the best price in each direction. In the example above, several carriers are offering cheaper outbound flights, such as these on Southwest Airlines (to Midway Airport instead of O’Hare):
Even when prices are roughly equal, having more flight options means you can be choosier about when you fly, which airport or terminal you use, and even where you sit. Finally, booking award segments individually is helpful if your travel schedule isn’t totally locked in. As plans shift, you can adjust one end of your itinerary without disrupting the other.
You can sometimes save by booking separate trips (or portions of separate trips) such that they overlap — that is, by “nesting” one trip inside another. This is most commonly beneficial on routes you fly often, since the frequency creates more opportunities for nesting.
Imagine you need to book two trips from Atlanta to Los Angeles, one in September and one in October. With conventional framing, you might book the following two round-trip itineraries outbound from Atlanta and returning to Los Angeles, at a total cost of 119,600 Delta SkyMiles and $22.40 in fees:
Alternatively, you could nest one trip inside the other. In this framing, one “trip” consists of the first outbound flight from Atlanta and the last return flight from Los Angeles, while the nested “trip” consists of the first return flight from Los Angeles and the second outbound flight from Atlanta:
These combined itineraries are functionally identical to the originals — same airline, same flights, same class of service — but they cost 110,900 miles and $22.40 in fees instead, saving you 8,700 miles. That’s not to say any of these flights are a good deal, but the nested flights are inarguably a better deal than the originals.
Nested flights can have multiple layers. If the example above also involved trips in November and December, pursuing a discount might lead you to a string of intertwined itineraries:
Itinerary 1: September outbound + November return.
Itinerary 2: September return + December outbound.
Itinerary 3: October outbound + December return.
Itinerary 4: October return + November outbound.
The downside of fishing for discounts this way is the complexity it adds to travel plans. Changing or canceling reservations gets messy when each itinerary involves flight segments pertaining to multiple trips. Even keeping track of confirmation numbers and other basic details can be challenging, so make sure you have a good organizational system in place before you take this approach.
Combine ‘trips’ with multicity itineraries
Whereas a round-trip takes you from A to B and then from B back to A, a multicity itinerary involves additional destinations. Most airline websites offer multicity award searches, so you don’t need special access to look for them. Multicity awards often cost the same as their constituent parts, but not always. For example, imagine you live in Portland, Oregon, and plan to visit Nashville in November and then Las Vegas in January. Rather than book round-trip flights to each city, you could book one-ways on either end (Portland to Nashville and Las Vegas to Portland) with a multicity itinerary in the middle. In this case, Alaska Airlines is offering a multicity award for 17,500 Atmos Rewards points and $11.20 in fees.
If you booked those same flights as separate one-way awards, you’d pay 15,000 points for the Nashville to Portland flight plus 7,500 points for the Portland to Las Vegas flight. That totals 22,500 points, so booking a multi-city itinerary saves you 5,000 points in this case.
Multicity itineraries come in all shapes and sizes, such as the following examples.
A-B-C | Honolulu – San Francisco – Salt Lake City.
A-B-C-A | Miami – Kansas City – Houston – Miami.
A-B + C-A | Miami – Kansas City + Houston – Miami.
A-B-C-D | Phoenix – Boston – Dublin – Amsterdam.
A-B + C-D | Detroit – Frankfurt + Munich – Denver.
Note the distinction between the second and third examples: one includes a flight between Kansas City and Houston, while the other does not. Also note that “A” doesn’t necessarily represent home in these examples. If you reframe your travel such that home is simply a place you stop on the way to wherever you go next, then home could just as easily be any of the other destinations.
Make the rules work for you
Many frequent flyer programs offer award charts and routing rules with sweet spots you can exploit to maximize the value of your miles. Here are some routing strategies you can explore when hunting for a bargain.A stopover is essentially a long connection that allows you to spend time in a destination you might otherwise see only from the airport. Some frequent flyer programs let you add complimentary or inexpensive stopovers onto eligible award flights, and in some cases you can add multiple stopovers onto a single ticket. Some stopovers can be months long so you can work them into your annual flight plans.
An open jaw is a specific type of multicity ticket for which either the origin or destination (or both) differs on the outbound and return portions. The multicity itinerary above (from Nashville to Portland to Las Vegas) is one example of a discounted open-jaw itinerary. However, frequent flyer programs may disallow certain open-jaw award routing or nullify potential savings by pricing open-jaw awards the same as their constituent one-way parts.
These various approaches to booking award flights aren’t mutually exclusive. You can use each one independently or combine them as your travel plans and award availability demand. The key is to approach booking with the understanding that all these options are on the table.
For example, suppose you live in Minneapolis and your travel plans for the rest of the year include (in order):
A wedding in San Diego.
A business trip to Charlotte.
A vacation to Madrid.
A family visit to Pittsburgh for the winter holidays.
Another business trip to Charlotte.
Using the strategies above, you might end up with the following itineraries in lieu of a series of round-trips:
Minneapolis – San Diego (one-way).
San Diego – Minneapolis – Pittsburgh (multicity with stopover).
Minneapolis – Charlotte – Minneapolis (round-trip).
Charlotte – Minneapolis – Charlotte (nested round-trip).
Minneapolis – Madrid + Pittsburgh – Minneapolis (open jaw).
Madrid – Minneapolis (one-way).
This example isn’t based on actual award searches; instead, it’s meant to give you a sense of how you might approach a series of awards. Once you get used to reframing your travel plans, you’ll find opportunities to save.
How to maximize your rewards
About the author
Peter Rothbart is a credit card connoisseur and award travel guru based in Seattle, Washington. A former aerospace engineer and long-time touring musician, he is now a freelance writer, covering a wide range of topics from travel and personal finance to art, sports, and human interest stories. His work has been featured at outlets such as Yahoo, Business Insider and The Points Guy.
