Your Umpteenth Reminder To Take Advantage of Award Routing Rules

this applies to United MileagePlus award tickets, which are relatively flexible (and generous)

my parents wanted me to go with them to Japan this fall, and well, if my nearly-million-miler-mom is going to pay for my award ticket, dōmo arigatō misutā robotto! regardless of where those miles are coming from, though, use them to your advantage by visiting more places for the same price. some people advocate tacking on a free one-way at the end of a round-trip or a stopover (Million Mile Secrets has a nice summary of your hacking options), but my favorite tactic is what i call the two-destination-plus.


Thanks mom for the award ticket! I used my own miles to upgrade the outbound to business class. According to the 1K agent who helped me change my ticket, the upgrade only applies through to Seoul, not through to Tokyo.

the two destinations

because United allows you a stopover on your way to or from your destination, you can effectively see two cities for the price of one. in this case i’m stopping over in Seoul (destination 1) for a week on the way to Japan (destination 2), where I’m taking advantage of the open-jaw rule whereby i don’t have to fly back from the same city i flew into — in this case, i’m flying into Tokyo but returning from Osaka.

the plus

you’ll notice, though, that i have a layover in Shanghai (the plus) on the way there. it occurred to me today that i can hopefully finally knock the Shanghai maglev off of my bucket list (which i’ve been threatening to do for a long time now) so why not change my outbound flight to Seoul from a bleh couple hours at LAX to an overnight in Shanghai so i can ride the maglev? the beauty of this is that a layover — i.e., a break in your travel plans of less than 24 hours — doesn’t count as a stopover. if you can time it right so your inbound and outbound flight are just under 24 hours, score! you can do this multiple times if you can find workable flights. tack a couple cities on!

sidebar this is one of the benefits of being a Platinum or higher elite level member with the program: free award ticket changes. i probably would have paid the change fee for this otherwise, but even better than that? better planning — that’s free! [lesson learned!]


just choose the “Multiple Destinations” option when searching for your award ticket. the system will complain with a generic error if your routing isn’t valid, and sometimes it won’t show you all the flights that are available. for better results, do your searches as multiple one-ways, which i’ve found may show more flights, and call it in and tell them the website wouldn’t book it properly in hopes they waive the ticketing fee if you don’t qualify for an elite-freebie. in my experience, though, the Multiple Destinations search works decently well.

i have been able to book award tickets to Asia via Europe, though this may or may not be available any more, but how great is that, to get a trip to Europe with your Asia trip (or a trip to Asia with your Europe trip)?

more examples

all of these real examples are the same price as a plain ol’ round trip. these are award reservations i have for later this year:

A One-Destination-Double-Plus with Getaway (more about Getaways later)

  • Thursday: San Francisco → London (arrive 12:15 PM Friday) — redeye so i am not missing any work (thanks to being on east coast hours though i’m on the west coast, i have late afternoons free)
    • spend the afternoon and night in London working (again, east coast business hours, my workation modus operandi)
  • Saturday: London (depart 7:05 AM)  → Oslo — this is less than 24 hours so it counts as a layover
    • (Getaway week in Iceland, flights there on a separate ticket)
  • Saturday: Oslo → Los Angeles (arrive 9:23 PM Saturday)
    • spend Sunday at my cousin’s graduation (which I would have bought a plane ticket for anyways)
  • Sunday: Los Angeles → San Francisco

A Two-Destination

  • San Francisco → Amman
    • knock Petra off my bucket list
  • Amman → Dubai
  • Dubai → San Francisco

examples from past trips:

A Two-Destination-Plus (though i could have easily gone into town on my last layover)

  • Friday: San Francisco → Taipei (arrive early Sunday morning)
  • Sunday afternoon: Taipei → Singapore
  • Thursday: Singapore → Yangon
  • Saturday redeye: Yangon → Tokyo
  • Sunday: Tokyo → San Francisco

A Two-Destination

  • San Francisco → Penang
  • Penang → Hong Kong
  • Hong Kong →  San Francisco

A Two-Destination-Plus (where i actually did spend a day in Tokyo)

  • Wednesday: San Francisco  →  Bangkok
  • Monday: Bangkok  →  Ulaanbaatar
  • Saturday: Ulaanbaatar  →  Tokyo
  • Sunday: Tokyo  →  San Francisco


you can add on a third destination (like Iceland above) if you can find a cheap flight — not a hard task given the proliferation of low-cost carriers (or just plain cheap flights) that are out there.

here’s an example of a two-destination with getaway: i flew from San Francisco to Hamburg (destination 1) and spent a handful of days there going to concerts (with a side trip to Copenhagen via train), then flew to Istanbul (destination 2) where i, says the award ticket, spent over a week. but little did United know, i bought a cheap ticket to fly to Kiev (with a side trip to Chernobyl) for four days (the getaway). sure, i had to fly back to Istanbul for my flight home, but three countries (not including Denmark) for 65,000 miles and a couple hundred dollars? yes, please. and please, make your miles work harder — take advantage of what basically amount to free-er trips on your free trips!

3 Comments on "Your Umpteenth Reminder To Take Advantage of Award Routing Rules"

  1. Be sure to check out the koyo if you can

    You can also get a Hello Kitty Icoca if you get the visitor Haruka + Icoca pass. Alas, it is only available at KIX for pickup.

    T-Mobile Simple Choice Roaming works for China, South Korea, and Japan. Getting a SIM in Japan is a bit on the expensive side though possible for data only. S. Korea now allows visitor sims without 3 day residency.

    There are some really neat sightseeing trains in Japan. Check jprail
    Personally, I’d love to ride the Seven Stars in Kyushu (great trains & service on JR Kyushu overall) and the A Train

    • thanks for the tips! yeah, the first time i went to Japan i had free (well, sort of) int’l roaming through our work account, but subsequent times i’ve either rented a SIM (so $$$) or lived without. can’t wait to finally try t-mo int’l roaming next week in Ireland!

      and yes, my first trip was also during the fall and i *loved* the fall foliage, though perhaps not as much as the local leaf peepers who set up cameras and zoom lenses and waited to get just…the…right…shot! i think my parents seeing pictures of that convinced them to make a trip in the fall. i’m not sure how railfan my parents are, though, but i’ll see if i can squeeze in some of those that you recommended! i really liked the hakone loop, maybe i’ll suggest that as well.

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