Stopover Magic: How To Book Two Trips For The Price Of One!

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How To Book Stopovers

Guide: How To Book Stopovers, 2 Flights for the Price of One!

One of my favorite ways to get extra value from my miles is by utilizing stopovers. It’s extremely satisfying to book an award to two destinations for the same price as one. I’ve done this a few times, including a spring trip when my son and I visited both Seattle and Boise. Another time was when we flew Cathay Pacific premium economy followed by long-haul business class with a stopover in Hong Kong. That whole trip was a fantastic adventure with two of my kids. I wanted to share a guide with you on how to book stopovers so you can maximize your award miles too.

Not only that, there is even more magic that you can unlock with stopovers. Rather than just booking a ticket to two destinations, how about using the stopover rules to book pieces of two different trips as a single award? You’re essentially getting two trips for the price of one. I’ll show you how this magic works.

The Key: One-Way Stopovers

Most airlines offering stopovers let you add them on round-trip awards. There are two notable exceptions: Alaska Airlines MileagePlan and Cathay Pacific Asia Miles. Both of these programs let you add stopovers on one-way award tickets, making them ideal for booking two trips for the price of one. The secret is selecting your home airport as your “stopover”. Your end point becomes your mid-point, and suddenly you have half of two separate trips booked.

With each of these options, there is no limit to the amount of time you can spend at your stopover. You could book the inbound flight for a trip next month, and then the next segment 10 months later. You’re only constrained by the available schedule. At the risk of spoiling my whole section on Alaska, here is an example:

You fly the Honolulu to LAX segment in October, followed by the LAX to JFK segment next May. Not bad for 15,000 miles!

Beyond the one-way stopover options, there are a couple other currencies where you can get very creative. But let’s tackle Alaska MileagePlan first, my favorite for booking one-way stopovers.

How to Book Stopovers with Alaska Miles

There is no currency more useful than Alaska miles for utilizing stopovers to book two different trips. As I mentioned, the key is to plan the stopover in your home city (or a nearby city that you can either drive or position to).

Alaska multi-city search is especially easy to use for booking such an award. You do need to know what is allowed and what is not (if you keep getting error code -1580, your routing is likely the problem). Most of the time the stop needs to be in a major “hub” city.

I live in northern California, and we often fly out of San Francisco International Airport. Maybe I’m planning a return trip to Hong Kong and want to fly Cathay Pacific business class on the way back to California. Booking an award from HKG to SFO is fairly easy over the phone with Alaska, as long as I can find available space.

But what if I’m planning to visit NYC a couple months later? Alaska doesn’t charge any more miles if I wanted to add a SFO-EWR segment. Could we plan a “stopover” in San Francisco? Absolutely yes.

How To Book Stopovers map
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.

Voila. Two awards for the price of one. Even if the SFO-EWR segment is in coach, I just saved 12,500 miles. The total cost of the ticket would still be 50,000 Alaska miles. If I score first class across the continent, that’s just a bonus.

Consider the following as another example: I’m looking at planning a trip to Hawaii early next year, followed by a visit to England later in the Spring. Business class flights between the U.S. and Europe start at 55,000 Alaska miles. But for the same cost, you can fly first class home from Hawaii (economy only on the SEA-LAX leg), continuing onto Europe on the same award after your “stopover”. Here I quickly found the business space with British Airways:

Two Trips For The Price Of One - Alaska Stopover

Sure, this is going to hurt due to the British Airways fees, but the same logic applies for booking American Airlines (or other European partner) flights. You could be paying just 57,500 miles and $23.70 for this award!

Takeaway: if you live in/near an Alaska hub (you can even make things work at an American hub), plan a stopover in your home city to get two trips for the price of one.

How to Book Stopovers with Asia Miles: The Best Transfer Option

If accruing enough Alaska miles is a perennial problem, consider turning to Cathay Pacific Asia Miles. You can amass Asia Miles easily by transferring Membership Rewards or Citi Thank You points.

Asia Miles lets you book a single stopover on one-way awards using the standard award chart (Cathay + 1 partner, at most). You’re limited to two sectors, which means that your layover point simple has to become your stopover point. While this sounds limiting, it isn’t quite as big of an issue as you might think.

The following itinerary as a simple example:

Singapore (SIN) – Hong Kong (HKG) – Los Angeles

I found space for this quickly and easily using the multi-city booking tool on the Asia Miles website. I got as far as selecting the second flight, but with insufficient miles in my account, I cannot go any further. You can easily see the date of the first flight is January 15, 2020, with the following segment on March 19.

How To Book Stopovers

If you live in Hong Kong, this is a great way to get two trips out of a single award (business class is 85,000 miles). But obviously most of us don’t live in Hong Kong. Let’s try another example:

Hong Kong (HKG) – New York City (JFK) – Amman (AMM)

If you’re a New Yorker, this would let you fly back home from Hong Kong, stop indefinitely, and then continue on a separate trip to Jordan. This is available in business for just 90,000 Asia Miles (5,000 extra miles levied when partners are involved). It is a ridiculous 13,800 miles of flying!

Two Trips For The Price Of One - Asia Miles
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.

Not headed abroad? You could fly HKG-JFK(stop)-LAX. You won’t be able to book this award online (AA space doesn’t show), but it is still a completely valid routing. You’ll pay 90,000 miles to fly this itinerary in business, which is not a bad deal, especially if you can score American Airlines’ premium business on the flight to LA!

How to Book Stopovers with United MileagePlus & Being Creative

I want to touch on the power of the United Excursionist Perk. While most people use it as a stopover on a round-trip award, it is actually far more useful. The way the rules work allows all kinds of crazy flexibility.

Have you ever considered booking a short-haul award in another (non-US48) award region for just 8,000 United miles? Well, if you have, just know that you can get a free one-way ticket out of the deal. The United Excursionist Perk requires that you book a round-trip ticket beginning and ending in the same zone. Your free segment must then simply be within one zone. Check out this itinerary:

  • Panama City (PTY) to San Jose, Costa Rica (SJO) for 8,000 United miles
  • Arcata (ACV) to San Francisco (SFO) to Boston (BOS) for 0 miles (Excursionist Perk)
  • Unnecessary short-haul throwaway segment in Central America

The total cost of the award: 16,000 United miles. Instead of getting that domestic U.S. award for 12,500 miles, you essentially just booked it for 8,000 miles, saving 4,500 miles. If you actually need a one-way in Central America later, you just saved the full 12,500 miles.

Two Trips For The Price Of One - United

Don’t believe me? This itinerary easily prices out how I’ve explained. Here I have flights a week apart, but the stopovers can be of any length through the end of the United calendar. Only annoying thing is the Central American airport taxes and fees.

How To Book Stopovers United

The flight order is important. Your Excursionist Perk segment must be sandwiched between your round-trip. Again, the last segment can be a throwaway, or you can plan it into a third trip.

You Cannot Beat Two Trips For The Price Of One

There are other great ways to creatively plan stopovers for maximum value, but I find that these are three of the best. The massive flexibility of one-way awards with both Alaska MileagePlan and Asia Miles lets you book half of two different trips as a single award. I’ve barely tapped the potential of the United Excursionist Perk, but there is a ton of potential there for booking two trips for the price of one as well.

Have you ever creatively used a “stopover” to book parts of two different trips as a single award ticket? I’m curious to know what readers have pulled off.

Ian Snyder
After igniting his passion for award travel while planning his honeymoon, Ian now enjoys using points and miles to see the world with his wife and three internationally adopted kiddos. He loves dissecting loyalty programs to find maximum value. His goal is to demonstrate that extraordinary travel is possible for the ordinary family.

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  1. Ian – I thought I was following your instructions till the book your home as the stopover comment.
    Here is my situation, I live in Houston, I have plenty of Alaska miles, I also have companion pass.
    If I drive to Austin, I can go on miles/points

    AUS – SFO – spend a week in SFO
    then SFO -SEA – spend 4 weeks from Seattle to Vancouver riding our bikes through the San Juan Islands
    then fly back
    YVR-PDX – spend a week in Portland then
    PDX- AUS
    Doing this on Saturdays will cost me 40K miles + about $107US total
    We are retired so have time.
    With Companion pass, same itinerary $580 Total
    I did this out of Austin, because it was not possible out of Houston.
    Would the above be using a stopover for Free?
    In order to use stopover at your home airport be that you have to be somewhere else first?
    Hope this is not too complicated.

    • Hi Robert,

      You just want to do a more “traditional” stopover. What you’ve described is *entirely* possible. You are maximizing Alaska’s stopover rule, using one on each “leg” of the trip (stopover in SF on outbound to SEA, stopover in Portland on return to Austin).

      What I’ve presented here is the option to add a segment as part of another trip, if you *weren’t* planning on using a stopover n your award.

      Hope you get that booked! It sounds absolutely amazing.

      • Ian -It looks like ALASKA is letting me do the itinerary, but I want to see about in the future using your strategy
        if I understand your info – lets say Im in Madrid because I did a oneway some time ago, then I could book Madrid to Houston(home) then later on down the like do Houston to ??Where-ever – That way I can get my flight home paid for plus the beginning of another future trip.

        • Houston may not work, as you typically need it to be a hub or major connection of Alaska partners. But Dallas may work. Example:

          MAD-DFW on AA/IB (end of first trip)
          (stopover for however long you want)
          DFW-SFO-HNL on AS (beginning of second trip)

          All booked as a single one-way award.

  2. So what’s the best airline and route to get from Albany NY with a stop in los Angeles and then Vegas and back home?

    • On a round-trip, you could still get away with using Aeroplan miles to do that to fly United. If you can piece this together with Alaska and American flights, you could also book it with Alaska miles (LAX will qualify as an AS hub for your stopover). As AS doesn’t fly to Albany, some flight sill obviously need to be AA-operated.

    • Unfortunately, I will not be. Wish I could make it. Every year I’ve said “next year I’ll go”. Saying the same this year. One of these days!


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