
Introduction
In my last honeymoon post, I shared how I booked two business class seats on Japan Airlines using Alaska Airlines miles. One of the main benefits of booking award tickets with Alaska Airlines is the ability to add a stopover. With this benefit, you basically get to see a second city for a negligible increase in taxes/fees and miles. Here’s how we made use of Alaska Airlines’ free stopover with a flight from Tokyo to Singapore.
Alaska Airlines Free Stopover
Here’s a breakdown of the basics of Alaska Airlines free stopover as it applied to our flights:
- You get one stopover per one way ticket
- Stopovers are generally in the hub city since the stopover has to be in a logical route to the final destination (Tokyo served as our stopover city)
- You can’t combine multiple Alaska Airline partners when booking a stopover (our flight to and from Tokyo had to be on Japan Airlines)
- The stopover can be in a third region that is different from your origin and your final destination (our origin [JFK] is in the U.S., our stopover [Tokyo] is in Japan, and our final destination [Singapore] is in Southeast Asia.)
Booking Your Free Stopover with Alaska Airlines
If the dates of the flights to and from your stopover are available, you can book the entire itinerary at once. However, I had to book our flights from JFK to Haneda the day they were available to make sure I got the business class seats I so desperately wanted (more on that here). Had I waited for the Tokyo to Singapore flight to become available 10 days later, I’d have missed out on the seats to Tokyo.
Luckily, you can easily add a stopover at a later date by calling Alaska Airlines. If it is more than 60 days prior to departure, there will be no fee for making a change to your itinerary.
My Experience Booking My Free Stopover
Alaska Airlines agents are very competent, but these calls can sometimes take a while due to the weird things that happen with clunky airline systems. To update the ticket, the agent had to take back control of the itinerary from Japan Airlines and then make the change. For some reason my fiancĂ©’s ticket “failed”, so it had to be processed manually. According to the agent, the ticket failure can occur if the network drops for even a split second. She decided to call me back while she worked on fixing the issue. After about 30 minutes, she called back saying that while she was troubleshooting the messed up ticket, it ended up updating on its own. She also noted that this issue occurred because we were flying to a different region than that of the stopover city.
I went to check the itinerary and saw she booked the ticket for the wrong day! (I already said they’re competent and stand by that…I think she may have misheard me.) I was afraid when I called back the same ticket failure situation would happen, but the agent was able to rebook for the correct day in a matter of minutes.
Our flights were an extra 5,000 miles per person since we were traveling to a different region than our stopover (Japan to Southeast Asia). The additional fees were $23 per person. You can’t beat that for two business class tickets on an 8-hour flight!

Final Thoughts
The free stopover perk is the main reason I chose Alaska Airlines for our flights to Tokyo and on to Singapore. Even if you already booked a one-way flight using Alaska Airlines miles, it’s possible to treat the initial destination as a stopover if it’s in the hub of the airline you’ll be flying. With one *hopefully* quick phone call to Alaska Airlines, you’ll get to see an extra city for close to the price of your original itinerary. For us, this stopover perk got us two business class seats valued at just under $7,000 for an additional 10,000 miles. You can’t beat that with a stick (I’ve never used this expression before, but I feel like it fits here).
Honeymoon Stats
Points spent: 865,000
Out-of-pocket cost: $1,404.93
Total value: $37,449.22
Congrats! I’ve always wanted to fly JAL or ANA. Was there no availability for first class or did you not have enough points?
Thank you! This plane only has two cabins so business class is as good as it’s going to get.