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The complete guide to maximizing stopovers and open jaws on award tickets

March 18, 2021
38 min read
Alaska and American planes on the runway at LAX
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If you're reading this post, chances are you're interested in making the most of your hard-earned points and miles. For many, this involves splurging on fantastic first-class flights or luxurious hotel rooms.

However, others may be interested in traveling to and visiting more than one city on a single trip, and one of the best ways to do this is by including stopovers and/or open jaws on your award flights. You can use these rules to book a tour of Europe or Asia, or in some cases, use your open jaw and stopover rules to create a mini-round-the-world itinerary.

Today, I'll discuss stopover and open jaw rules for each of the major airlines to help you maximize your redemptions in 2021. I'll discuss what stopovers and layovers are and then dive into rules for each major loyalty program.

Let's get started!

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What Are Stopovers and Open Jaws?

(Photo by Alex Tai/SOPA Images/LightRocket/Getty Images)

So, what are stopovers and open jaws? Good question.

Let's begin with a stopover. In short, this is a stop en route to your final destination. This is different than a connection, which typically is just a brief layover in an airport. Think of it as hitting pause on your itinerary. Generally speaking, any stop of more than four hours on a domestic itinerary and more than 24 hours on an international itinerary is considered a stopover rather than a connection (this may vary by airline).

Open jaws work a bit differently. There are three different types of open jaw itineraries, so it's easier to illustrate these options on a map. I love using Great Circle Mapper for this purpose. It shows the geography and calculates the distances of your flights (great for distance-based award charts).

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Here's a look at the type of open jaws that are out there.

1. Fly from City A to City B, then fly from City C back to City A.

In this case, the destination on your outbound flight (B) is different than the city you use to return home (C). The open jaw is between City B and City C, and it's up to you to "fill in" that open jaw with your own land, air or sea travel.

Here's an example from Washington-Dulles (IAD) to London-Heathrow (LHR), then returning to IAD from Paris (CDG):

(Image courtesy of Great Circle Mapper)

2. Fly from City A to City B, then fly from City B to City C.

In this case, your departure gateway (A) is different than your final arrival city at the end of the trip (C). Once again, it's up to you to "fill in" that open jaw between City A and City C.

Here's an example of a flight from Los Angeles (LAX) to Sydney (SYD), but instead of returning back to LAX, you instead fly back to San Francisco (SFO):

(Image courtesy of Great Circle Mapper)

3. Fly from City A to City B, then fly from City C to City D.

In this case, you have a double-open-jaw. You need to make your own way from City B to City C during the trip and then make your own way from City D to City A at the end of the trip.

Here's an example of a double open jaw within the US, flying from Philadelphia (PHL) to Chicago-O'Hare (ORD) on the outbound and then returning from Des Moines (DSM) to Washington-National (DCA).

(Image courtesy of Great Circle Mapper)

In most situations, it's important to note that an open jaw isn't totally flexible. To qualify as a valid open jaw, two conditions must typically be met:

  • The open jaw needs to be within the same region (defined by each airline's program).
  • The unflown segment needs to be shorter than the distance of the flown segments.

As a result, while any of the above itineraries would be valid open jaws, here's an example of an invalid one:

(Image courtesy of Great Circle Mapper)

In this instance, both rules are violated: The distance of the unflown segment (Santiago to New York-JFK) is greater than one of the flown segments (New York to London-Heathrow) and the open jaw spans two regions (North America and South America).

Related: How I booked a round-the-world ticket in business class for 170,000 miles

Can't You Just Create Open Jaws With Multiple One-Way Tickets?

(Photo by aapsky/Shutterstock)

Technically, yes, this is correct — the vast majority of carriers allow you to book one-way awards. Even if your desired airline doesn't allow open jaws, you could create your own open jaw by booking a one-way award ticket from City A to City B and then book another one-way ticket from City C back to City A.

That said, you may not want to do this. Here are a few reasons why this may not make sense:


As you'll see below, many carriers do not allow stopovers on one-way tickets, so you must book a round-trip award ticket to qualify. Note that an itinerary with an open jaw typically does count as a round-trip ticket, even though there are multiple cities involved.

Change fees

I'm sure many of you have been forced to pay change or cancellation fees before. If you need to cancel your trip and have booked two one-way tickets, you could be looking at double the fees. While many of these fees have gone away, it's still important to mention — especially if booking with a foreign carrier.

Origination surcharges

Other carriers tack on fees when you begin your trip in certain regions. For example, Delta adds a "carrier-imposed international surcharge" when you start an award itinerary in Europe. This is generally in the neighborhood of $100-$150 for economy and $150-$200 for business class. However, you'd avoid this by booking a round-trip award flight.


The final reason why booking one-way award tickets may not make sense is if you're traveling with an infant-in-arms. Most carriers require you to pay 10% of the adult fare when you travel internationally with a lap child, and one-way tickets can often be exorbitantly expensive. I've seen many cases where the price of a round-trip flight is less than half the price of one of the legs booked as a one-way.

Related: Can I book an open jaw or stopover on ANA with Virgin Atlantic miles?

Stopover and open jaw rules for major airlines

Air Canada Aeroplan has some of the most relaxed stopover and open jaw rules. (Photo by Heather Dunbar/Shutterstock)

Now that you understand these two terms, let's take a closer look at the major carriers' policies surrounding stopovers and open jaws. I'll start with an overview table that'll provide a snapshot of your options. I'll then follow up with additional details on each one, along with some suggestions for how you can accrue miles or points in that program.

These programs are transfer partners of at least one of these currencies:

Here's a high-level overview of these policies:




Open Jaw(s)

Valid One-Way?

Other Important Notes






Very flexible routing rules.






Stopovers are only valid at limited international gateways/partner hubs.






You can create open jaw(s) by booking one-way flights.






Only valid on certain awards.

British Airways





Distance-based award chart.






You can create open jaw(s) by booking a multi-city itinerary.

Japan Airlines





Number of stopovers depends on the airline you're flying.





Only on full/standard awards

Varies depending on your award type.






Book via the Excursionist Perk

Now let's get down into the nitty-gritty:

Related: What’s the difference between connections and stopovers?

Air Canada Aeroplan

(Photo by Vytautas Kielaitis/Shutterstock)

Aeroplan was completely revamped last year, with a new award chart and stopover rules. The new program lets you add a stopover to any one-way ticket for 5,000 points and up to two stopovers to a round-trip ticket for 5,000 points apiece. You're also allowed an open jaw to your ticket, but only between one-way flights and not between connecting cities or stopovers.

One of the best parts about Aeroplan's new stopover rules is that there's no maximum mileage or too many set routing rules. The only thing to keep in mind is that your stopover ticket cannot be more than twice the mileage of a nonstop ticket to your final destination. This means something like New York-JFK to Abu Dhabi (AUH) to Frankfurt (FRA) isn’t bookable on a one-way ticket.

There aren't any set restrictions on transiting via a third region either and you can mix partners. So on a round-trip ticket, you can use this to create amazing round-the-world itineraries — especially when combined with strategic 24-hour layovers. Here's a quick example I thought up:

(Image courtesy of Great Circle Mapper)


  • Chicago-O'Hare (ORD) to Frankfurt (FRA) - Layover, Lufthansa
  • Frankfurt to Prague (PRG) - Stopover, Lufthansa
  • Prague to Warsaw (WAW) - Layover, LOT Polish Airlines
  • Warsaw to Beijing (PEK) - Final destination, open jaw, LOT Polish Airlines


  • Seoul (ICN) to Tokyo-Haneda (HND) - Stopover, Asiana business class
  • Tokyo to Los Angeles (LAX) - Layover, ANA business class
  • Los Angeles to Chicago - Final destination, United domestic first class

You'll see here that — on the outbound — we fly from Chicago to Beijing via Europe. While in Europe, we have a day-long layover in Frankfurt, a stopover in Prague and another day-long layover in Warsaw. Once in Beijing, we can spend as long as we'd like in the city and take a cheap flight to Seoul. Then, we'd start the return ticket by flying to Tokyo for a stopover. We'll return to the U.S. on ANA by flying to Los Angeles for a layover before flying to Chicago on United.

Air Canada stopover restrictions

Here's a quick look at all the rules to keep in mind:

  • Stopovers cost an additional 5,000 points
  • You can add one stopover per one-way ticket
  • No stopovers in the U.S. or Canada
  • You can have up to six segments per one-way ticket
  • You cannot book tickets that are 100% or more physical miles over the direct distance between two cities
  • Itineraries within a single region must stay within said region.
  • There are no Maximum Permitted Mileage restrictions for flight rewards on partners
  • Open jaw tickets are only permitted between one-way tickets, not between connecting cities or stopovers
  • All flights are priced on a one-way basis

It's also worth noting that Air Canada no longer adds fuel surcharges to award tickets. Further, awards are priced based on the physical distance and the region you're flying to and from. Check out our full guide to the Aeroplan award chart for more info.

How to book stopovers and open jaws with Air Canada

You cannot book tickets with stopovers online, so call Aeroplan once you've found award space. Check out our guide to finding Star Alliance award space for more information.

Earning Aeroplan miles: Transfer points from American Express Membership Rewards, Capital One or Marriott, or credit Star Alliance flights to Aeroplan.

Related: A guide to the new Aeroplan’s award routing and stopover rules

Alaska Airlines Mileage Plan

(Photo by Alex Tai/SOPA Images/LightRocket/Getty Images)

Alaska Airlines Mileage Plan offers some of the best value premium cabin redemptions, especially for travel to Asia. It also offers some generous routing rules with stopovers and open jaws. For international award tickets, you're allowed to have one stopover on each one-way flight and you can also utilize an open jaw.

However, the big restriction is the fact that you are restricted to one partner airline per award ticket (plus any Alaska flights to get to your international gateway). As a result, you can't fly from New York to London on British Airways and then return from Helsinki to New York on Finnair. Thankfully, you can skirt this restriction on round-trip itineraries by booking two one-way tickets since you can use different partners on the outbound and inbound tickets.

For stopovers outside the US, you're generally only allowed to stop in the hub of the partner airline you're flying. For Cathay Pacific, this would be Hong Kong (HKG) or Tokyo (NRT or HND) for JAL.

So with that in mind, you can book something like this:

(Image courtesy of Great Circle Mapper)


  • Seattle (SEA) to New York-JFK - Layover, Alaska domestic first class
  • New York-JFK to Dubai (DXB) - Stopover, Emirates business class
  • Dubai to Hong Kong (HKG) - FInal destination, Emirates business class


  • Taipei (TPE) to Tokyo-Haneda (HND) - Stopover, Japan Airlines business class
  • Tokyo to Seattle - Final destination, Japan Airlines business class.

Alaska Airlines stopover restrictions

To recap, here's a look at Alaska's stopover and open jaw restrictions:

  • You can add one stopover on each one-way international ticket
  • The stopover can be at the international carrier's hub
  • You cannot combine partners, but you can add an Alaska Airlines ticket to connect to an international gateway

While the blanket policy is that stopovers are only allowed on international award tickets, there are two exceptions. From the Mileage Plan Terms and Conditions:

"An exception allowing an otherwise-illegal open jaw trip is permitted when travel is between the State of Alaska and the lower 48 states and a stopover occurs in Southeast Alaska. When award travel is redeemed solely on Alaska Airlines, one enroute stopover is allowed for each one-way award."

How to book stopovers and open jaws with Alaska Airlines

You can book these stopovers online all by yourself for all Alaska partners except for Cathay Pacific and LATAM (where you need to call in to book any award). Simply check the "multi-city" box when searching and enter the dates you want, though I find it much easier to search segment by segment first to find the award space. Then you can perform a multi-city search when you've found your flights and are ready to book.

(Screenshot courtesy of Alaska Airlines)

Here's an example of an online search for a flight from Newark (EWR) to Bangkok (BKK) on Emirates with a long stopover in Dubai (DXB):

(Screenshot courtesy of Alaska Airlines)

You can earn Alaska miles by transferring Marriott points or applying for the Alaska Airlines Visa Signature® credit card. You could also buy miles during one of the program's frequent promotions.

Related: 5 things to know about Alaska Airlines Mileage Plan

American Airlines AAdvantage

(Photo by Zach Griff / The Points Guy)

In 2014, American Airlines eliminated the ability to include a stopover on AAdvantage award tickets, which was previously restricted to the international gateway. Despite this devaluation, you're still able to include an open jaw or two due to the ability to book one-way awards on American. American recently got rid of award cancelation fees too, so there's no downside to booking two one-ways instead of a round-trip award ticket.

Earning American miles: Transfer points from Marriott or spend on an American cobranded credit card.

Related: How to redeem miles with the American Airlines AAdvantage program

ANA Mileage Club

(Photo by TungCheung/Shutterstock)

ANA Mileage Club has been a longtime favorite of points and miles enthusiasts. This is in large part due to generous rates on awards for both ANA and partner-operated flights. While you're only allowed to book round-trip awards, ANA does allow stopovers and open jaws on certain eligible routes.

You're allowed one stopover on all ANA tickets, except for itineraries wholly in Japan. Likewise, on ANA flights, you're only allowed a stopover if your itinerary originates outside of Japan. Stopovers can either be on the outbound or inbound leg of your ticket and you're allowed an open jaw on both the inbound and outbound leg.

For example, you can book this without issue:

(Image courtesy of Great Circle Mapper)


  • New York-JFK to Istanbul (IST) - Stopover, Turkish Airlines
  • Istanbul to Odessa (ODS) - Final destination, open jaw, Turkish Airlines


  • Kyiv (KBP) to Warsaw (WAW) - Layover, LOT Polish Airlines
  • Warsaw to Chicago-O'Hare (ORD) - Final destination, LOT Polish Airlines

Related: How I’m booking a business-class trip to Turkey and Ukraine this spring

ANA Mileage Club stopover restrictions

Again, here are the key restrictions on stopovers and open jaws:

  • On domestic flights within Japan, no stopovers are allowed
  • On ANA-only international award tickets, you are only allowed one stopover on flights departing from overseas (no stopovers allowed for flights departing Japan)
  • On partner award tickets, you are allowed one stopover on either the inbound or outbound flight
  • You can include an open jaw at the start and end of the award ticket, as long as the two airports are in the same country
  • You can include an open jaw at the destination, as long as the two airports are in the same "area"

This last point is most confusing. ANA uses a zone-based award chart with 10 different geographical zones spread across the globe. However, those zones are arranged into three "areas" that apply to open jaws:

Area 1: North America, Hawaii, Central America, South America
Area 2: Europe, Middle East, Africa
Area 3: Japan, South Korea, China, Southeast Asia, South Asia, Southwest Pacific

Your open jaw must happen in the same area, though you can't have one between North America (including Hawaii) and South/Latin America.

How to book stopovers and open jaws with ANA Mileage Club

You can book stopovers with ANA Mileage Club on the ANA website. Just head to the award booking screen and click on the "multiple cities/mixed classes" option at the top of the screen. Then, enter your desired itinerary and click the orange Search button at the bottom of the page. You'll be presented with options for each leg on the following screens.

(Screenshot courtesy of ANA)

Here's a look at the sample itinerary discussed earlier:

(Screenshot courtesy of ANA)

Earning ANA miles: Transfer points from American Express Membership Rewards or Marriott.

Related: TPG Lemonade session: ANA Mileage Club

British Airways

British Airways technically allows unlimited stopovers thanks to its distance-based award chart, though you'll need to redeem separately for each leg. (Photo by Nicolas Economou/NurPhoto via Getty Images)

The British Airways Executive Club program can be viewed as either the most flexible or least flexible out there for stopovers and open jaws.

It follows a distance-based formula for calculating how many Avios you need for a particular award redemption. The total cost is based on the individual costs of your segments. As a result, you can build in as many stopovers as you'd like. However, since you're charged on a flight-by-flight basis, you'll wind up paying more to stop in London en route from JFK to Madrid (for example) than you would by flying nonstop from JFK to Madrid.

The only exception to this is when you're connecting to a destination in the U.K., as British Airways allows "free" stopovers in London before continuing onto a different city in England or Scotland. In fact, the BA search engine will even prompt you to include stopovers when you're searching for award flights:

(Screenshot courtesy of British Airways)

This can be a great way to visit London en route to another city like Edinburgh or Belfast without incurring any additional mileage cost. However, you'll likely wind up paying some additional taxes and fees.

How to book stopovers and open jaws with British Airways

If you want to take advantage of a free stopover in London when flying to another U.K. city, simply search for a flight to your final destination on the Book with Avios page. As discussed, the website will automatically ask if you'd like to add a stopover to your ticket.

(Screenshot courtesy of British Airways)

For all other bookings, simply search for one-way tickets on the Book with Avios website.

Earning British Airways Avios: Transfer from American Express Membership Rewards, Chase Ultimate Rewards and Marriott. You can also apply for the British Airways Visa Signature Card.

Related: 7 ways to earn miles for your next vacation without leaving the house

Delta SkyMiles

Booking open jaw itineraries with Delta can help you save cash and miles. (Photo by AaronP/Bauer-Griffin/GC Images)

While dynamic pricing is beginning to feel like the norm these days, Delta SkyMiles gets credit for this "innovation" several years back.

Even before the carrier removed its fixed award chart, it decided to eliminate stopovers and open jaws on award tickets. However, since Delta allows one-way award tickets, you can still build in either one or two open jaws by booking two different one-way award tickets on a single itinerary.

Doing this is a great way to avoid the carrier's absurd surcharge for award reservations that start in Europe. Plus, Delta usually charges more for one-way tickets than it does for round-trip or multi-city bookings. So in many cases, you'll save cash and miles when you book an open jaw instead of two one-way tickets.

Here's an example of an open jaw itinerary (built using's multi-city search). It costs 45,000 SkyMiles and $66.85 to fly from New York-JFK to London-Heathrow (LHR) and return from Amsterdam (AMS) to New York.

(Screenshot courtesy of Delta Air Lines)

Alternatively, you'd pay 56,000 SkyMiles and $5.60 on the outbound and 33,000 SkyMiles and roughly $227 in taxes and fees on the return ticket.

This means you save 44,000 SkyMiles and roughly $165.75 by booking this open jaw as a multi-city itinerary.

Earning Delta miles: Transfer from American Express Membership Rewards or Marriott, or apply for a Delta card like the Delta SkyMiles® Gold American Express Card.

Related: 5 things you need to know about Delta SkyMiles

Japan Airlines (JAL) Mileage Bank

JAL Mileage Bank has extremely flexible stopover rules. (Photo by Stanislav Kogiku/SOPA Images/LightRocket via Getty Images)

Japan Airlines (JAL) Mileage Bank is an intriguing option for stopovers and open jaws, especially since it uses a distance-based award chart for partner redemptions. However, the rules are a bit different for flights on JAL vs. flights on partner airlines.

On Oneworld award tickets, you can add up to seven stopovers and eight segments. I'll dive deeper into routing rules later, but as a general note, most itineraries are valid so long as you don't back-track to the itinerary's country of origin.

You can leverage these rules to create some pretty great itineraries, like this tour of Europe:

(Image courtesy of Great Circle Mapper)
  • Philadelphia (PHL) to Dublin (DUB) - Stopover, American Airlines
  • Dublin to London-Heathrow (LHR) - Stopover, British Airways
  • London to Helsinki (HEL) - Stopover, Finnair
  • Helsinki to Prague (PRG) - Stopover, Finnair
  • Prague to Madrid (MAD) - Final destination, Iberia
  • Madrid to Philadelphia - Return, American Airlines

Again, JAL uses a distance-based award chart for partner awards. The above itinerary clocks in at 10,294 miles flown, so it'd cost 60,000 miles in economy or 110,000 miles in business class. This is an excellent deal — just note that you have to pay fuel surcharges if your itinerary includes airlines that charge them. This includes British Airways and others.

JAL Mileage Bank stopover restrictions

JAL has different stopover rules for JAL-operated awards, Oneworld awards and awards operated by a single partner. Here's everything you need to know.

Stopover rules for JAL awards

These are the rules for award flights operated by JAL:

  • A maximum of three segments per award, each way
  • Only one Japan domestic sector is allowed each way of the journey
  • Award itineraries can’t include the original departure place or country as a transfer point to a different destination
  • The departure and return may be in different cities but must be in the same area and within the same country
  • The arrival city of the outbound journey and the departure city of the return journey may be in different cities but must be in the same area and within the same country

Stopover rules for Oneworld awards

These are the rules for awards operated by a mix of Oneworld partners.

  • Awards that combine Japan Airlines with partner flights fall under this award chart.
  • A maximum of eight segments per itinerary.
  • One surface (open jaw) sector is permitted in the whole itinerary.
  • A maximum of seven stopovers (a stay of more than 24 hours or surface sector) are permitted.
  • “One city” can be included three times at the maximum for the whole itinerary, but a stopover at “one city” is permitted only once in the whole itinerary.
  • A surface sector is counted to be “one stopover” regardless of the sojourn time.
  • The distance of the surface sector is included in the total distance of the award itinerary.
  • Two Japan domestic flight sectors can be included in the whole itinerary.
  • For itineraries originating in Japan, stopovers within Japan are not permitted.
  • One-way itineraries are permitted.
  • “Point of origin” and “final returning point” may differ, provided those cities are in the same country. (China includes Hong Kong and Macau.)
  • Itinerary via “Point of origin” is not permitted.
  • Itinerary via “Country of origin” is not permitted.
  • When different service classes are involved in one round-trip journey, the higher class's required mileage will apply.

Stopover rules for other partner awards

Rules for itineraries operated by a single partner (including non-alliance partners) are slightly different from Oneworld awards operated by 2+ partners. Keep these rules in mind:

  • A maximum of seven segments (excluding surface sectors) are permitted in the whole itinerary, except for the following airlines' awards:
  • Korean Air: a maximum of 2 flight sectors is permitted.
  • China Eastern Airlines: a maximum of 4 flight sectors is permitted. China domestic sectors are permitted for a maximum of 2 flight sectors.
  • Hawaiian Airlines: a maximum of 4 flight sectors is permitted. Hawaiian inter-island sectors are permitted for a maximum of 2 flight sectors.
  • Royal Air Maroc: a maximum of 4 flight sectors is permitted.
  • Vistara: a maximum of 4 flight sectors is permitted.
  • A maximum of three stopovers (a stay of more than 24 hours or surface sector) is permitted in the whole itinerary.
  • Stopovers in China are not permitted on China Eastern Airlines flights when international travel originates in China.
  • The rest of the restrictions are the same as Oneworld awards.

Note that when you redeem miles for award flights on partner airlines, you can book a one-way ticket and still take advantage of these stopovers, giving you a wealth of opportunities to tack additional cities on to your trip. This is a great option for booking Emirates first class, though JAL has added fuel surcharges to these awards that can top $1,000 for US departures. However, if you play around with your origin city, you can reduce these taxes considerably.

How to book stopovers and open jaws with JAL Mileage Bank

Oddly enough, JAL awards largely aren't bookable online. You'll want to find award space using a Oneworld search tool and then call the airline to book your award ticket. This can be time-consuming but well worth your time if you maximize routing rules for a high-value award.

Earning JAL miles: Transfer points from Marriott.

Related: First class showdown: Cathay Pacific vs. Japan Airlines

Singapore Airlines KrisFlyer

Singapore Airlines A380 First Class Suites. Photo by Brian Kelly / The Points Guy
Singapore Airlines A380 First Class Suites. (Photo by Brian Kelly / The Points Guy)

Even after a pair of devaluations to Singapore's premium class award rates and its partner award chart, there's no denying that Singapore Airlines has some incredible premium-class products (and TPG himself loves flying in Suites Class).

Singapore Krisflyer also gives you some flexibility to build in stopovers and open jaws on award tickets. Like many programs listed above, the exact policies vary depending on the type of award you book. If you are traveling exclusively on Singapore flights, you can have one stopover on one-way Advantage awards and two on round-trip Advantage awards. Saver awards — the cheaper option — is entitled to one stopover on a round-trip award, but none on a one-way. You can add additional stopovers for $100 apiece.

(Screenshot courtesy of Singapore Airlines)

For partner airlines, it gets a bit more muddled. You're allowed a complimentary stopover on a round-trip ticket and can pay $100 apiece for three additional stopovers.

You can also include an open jaw between the starting and ending cities or at the destination.

Singapore Airlines Krisflyer stopover restrictions

Make sure to keep these stopover restrictions in mind:

  • Stopovers are not permitted on a domestic itinerary, nor are they allowed within your country of origin on an international itinerary.
  • Stopovers are not permitted on itineraries solely within Europe or between the US, Canada, Puerto Rico or US Virgin Islands.
  • Stopovers are not permitted for one-way partner awards or one-way Saver awards on Singapore Airlines.
  • One origin or destination open jaw is permitted for a round-trip award.
  • Open jaws are allowed across different award zones, but the higher award level will apply.

How to book stopovers and open jaws with Singapore Airlines Krisflyer

You can book stopovers on Singapore Airlines-operated itineraries online, but partner awards with stopovers and all open jaw tickets must be booked over the phone. If you need to go the phone route, use your favorite Star Alliance search tool to find award space first and then call the airline to book. Going into the call with dates and flight numbers in-hand will make your booking experience far easier.

To add a stopover on Singapore Airlines, head to the airline's website log in to your Krisflyer account. Then, look toward the center of the airline's homepage, select the "redeem flights" button, and enter your itinerary. You'll want to enter your final destination and the dates you'd like to depart on your journey and return home. Click the blue Search button to view your search results.

(Screenshot courtesy of Singapore Airlines)

At the top of the search results, you'll see an "Add stopover" box. Click on this button and you can select which leg you'd like to add a stopover. You're limited to adding Singapore-operated stopovers online, so you'll see the airlines' fifth-freedom routes like New York-JFK to Frankfurt (FRA) and San Francisco (SFO) to Hong Kong (HKG). Simply add the stopover here and follow the on-screen prompts to finish booking your ticket.

(Screenshot courtesy of Singapore Airlines)

Earning KrisFlyer miles: Transfer points from Chase, Amex, Capital One, Citi or Marriott, making it one of the easiest currencies to earn.

Related: The best ways to get to Singapore using points and miles

United MileagePlus

(Photo by Nicolas Economou/NurPhoto via Getty Images)

While United MileagePlus doesn't explicitly permit stopovers or open jaws, it lets you create your own unique itinerary through the Excursionist Perk. If you're not familiar with this unique program, you should start by reading our complete guide to it, but here's the basic principle:

The first route wholly within a single MileagePlus-defined region that’s different than the region in which your itinerary begins and ends is free.

You can use this to create several stopovers and/or open jaws, and there's room to get very creative here given how few rules United has about the perk. I'll leave you with one simple example that incorporates a stopover, an open jaw and a free flight.

Here's a straightforward example of a flight from the U.S. to Europe with a stopover and an open jaw on the inbound leg:

(Image courtesy of Great Circle Mapper)
  • Houston (IAH) to Frankfurt (FRA) - Stopover, United Airlines
  • Frankfurt to Zurich (ZRH) - Destination, Lufthansa
  • Zurich (ZRH) to New York-JFK - Inbound flight, Swiss

This flight costs 63,000 miles in economy. The United flight to Frankfurt costs 30,000 miles, the Frankfurt to Zurich flight is free and Zurich to New York-JFK is 33,000 miles. The return flight is more expensive since it's operated by a partner airline.

Related: United raises partner award prices up to 10% after removing award chart

There are some more interesting ways to use this perk too. Say you're making two trips to Europe in the future and need connecting flights. You could book these with miles and — even if they're months apart — add a domestic U.S. flight in-between the two. For example, you can book something like this:

(Image courtesy of Great Circle Mapper)
  • Prague (PRG) to Frankfurt - Lufthansa
  • Chicago-O'Hare (ORD) to San Diego (SAN) - United
  • London-Heathrow (LHR) to Brussels (BRU) - Brussels Airlines

This entire itinerary costs 17,600 miles at the time of writing. The intra-Europe flights were 8,800 miles apiece and the Chicago to San Diego flight was free. This can be an excellent way to maximize your flights abroad, so keep it in mind when you start planning post-pandemic travel.

United MileagePlus stopover restrictions

There are a handful of restrictions to keep in mind when using the Excursionist perk, including:

  • The Excursionist Perk cannot be in the MileagePlus defined region where your travel originates. (For example, if your journey begins in North America, you will only receive the Excursionist Perk if travel is within a region outside of North America.)
  • Travel must end in the same MileagePlus-defined region where travel originates.
  • The origin and destination of the Excursionist Perk are within a single MileagePlus defined region.
  • The cabin of service and award inventory of the free one-way award is the same or lower than the one-way award preceding it.
  • If two or more one-way awards qualify for this benefit, only the first occurrence will be free.
  • Open jaws are allowed on all segments.

These are extremely relaxed rules and — as discussed — they can be worked in your favor.

How to book stopovers and open jaws with United MileagePlus

Using the Excursionist Perk to add stopovers is easy. All you have to do is head to United's website and click the "Advanced search" button in the middle of the page. Then, select "multi-city" at the top of the page and build out your desired itinerary at the center of the screen. Make sure to select the "miles" option at the top of the screen too.

(Screenshot courtesy of United)

Now, select your flights. You'll notice that your complimentary flight will price at zero miles so long as there's open award space. Remember, you can only fly in the same cabin (or lower) as the rest of your award ticket.

(Screenshot courtesy of United)

Now, follow the on-screen prompts to finish booking your ticket. If all goes according to plan and you followed all Excursionist Perk rules, you'll walk away with a free stopover.

(Screenshot courtesy of United)

Related: How to get maximum value from the United MileagePlus program

How to maximize stopovers and open jaws

(Photo by AaronP/Bauer-Griffin/GC Images)

Hopefully, you've seen how to begin taking advantage of stopovers and open jaws on award tickets, as many carriers give you valuable flexibility to extend the value of your miles. However, there are a few additional suggestions I have to help as you're planning your next trip:

1. Consider a connection of ~23.5 hours. When traveling internationally, most airlines will allow you to connect within 24 hours of your arrival and not count it as a stopover. If you can schedule an overnight layover that's close to 24 hours, you may be able to add yet another city to your itinerary without using up your stopover. I've done this in Brussels, London and Oslo in the past.

2. Add a "free" side trip. If you're already planning on redeeming your miles for a trip, why not look at adding a free side-trip courtesy of a stopover and/or open jaw? For example, say you want to vacation in Canada but also have a wedding to attend in Raleigh around the same time. Instead of booking two separate trips from Florida, you can fly from your home to Raleigh-Durham (RDU) (stop for a wedding) and then continue onto Montreal (YUL). After a week of vacation, you can return from Montreal to your home airport.

3. Diversify, diversify, DIVERSIFY. One of the best lessons I've learned in this hobby is the importance of diversification. By having multiple pots of mileage from which to choose, you have incredible flexibility in booking award tickets and filling in open jaws. This is why I love transferable point currencies and think that all award travelers should have them. These programs allow you to wait to transfer points until you are sure of your redemption needs.

Related: Airports that offer free city tours during long layovers

Bottom Line

Building in stopovers and open jaws on your award tickets can be a great way to make the most of your hard-earned points and miles and see a second city at no additional cost. If you're the type of traveler who lets the deals plan your trips, you can even use some of the restrictions (like Alaska only allowing you to stop in a partner's hub city) to begin mapping out your next trip.

I hope this post has given you a solid understanding of what these strategies are but also (more importantly) how to begin utilizing them across the major airlines. Safe travels!

Additional reporting by Nick Ewen.

Feature photo by AaronP/Bauer-Griffin/GC Images via Getty Image

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Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.