Cheapest way to book a flight with a long stopover

Cheapest way to

So you are thinking of making the most of a layover in a city you’ve never been to before by staying a few days to explore before heading to your final destination? Well, this post is for you!

For some people, layovers suck but for people with wanderlust, it is an opportunity to tick one more city off their list. This is a perfect opportunity for people like me who has a full-time 9 to 5 job and only gets two weeks of vacation a year. By extending a layover from a few hours to a few days, one can squeeze in a mini-vacation from your main vacation.

Take for example my situation. I am planning on going to the Philippines to visit my family in July for 17 days and I will be coming from Calgary. There is no direct flight from Calgary to Manila, there will always be a layover somewhere. I figured I would like to visit Tokyo on my way to Manila. Other cities I can choose to visit are Seoul, Hong Kong, or Taiwan. But I really want to visit Tokyo, so Tokyo is my first choice.

I have done my research to find out what the best way is to book my flight to include a side trip to Japan. Here are my options:

*To be consistent, I used for all of the options on here except for the last two options. In line with being consistent, I have chosen the cheapest flight that came up from the search results regardless of the airline. All flights on this post were searched on Dec. 15, 2015. All prices in this post is inclusive of tax and other fees. No businesses have paid me to write this post.

Option 1: Choosing the “multiple cities” tab when booking a flight

One can build an itinerary using the multiple destinations tab in It is pretty easy to use. There are five flight forms one can fill in. I started with Calgary to Tokyo (July 1) for Flight 1, Tokyo to Manila (July 7) for Flight 2, and Manila to Calgary (July 17) for Flight 3. The total price is CAD$2,210.

multiple cities option
Multiple cities flight starting from Calgary to Tokyo to Manila to Calgary

Option 2: Buy two round trip tickets

For option 2, I can do it in two ways:

Option 2.a I can book two round trip tickets with the first one being Calgary to Manila (July 1 to July 17) for CAD$1,540.34 and the second one being Manila to Tokyo (July 3 to July 7) for CAD$637.64. The total price of this option is CAD$2,177.98.

calgary to manila RT
Calgary to Manila round trip flight
manila to tokyo RT
Manila to Tokyo round trip flight

Option 2.b I can book two round trip tickets with the first one being Calgary to Tokyo (July 1 to 17) for CAD$1,572.10 and the second one being Tokyo to Manila (July 7 to 16) for CAD$575.96. The total price of this option is CAD$2,148.06. This is actually cheaper than Option 2.a!

c to t
Calgary to Tokyo round trip flight
t to m
Tokyo to Manila round trip flight

Option 3: Buy one way tickets for each city

Another alternative is to book each flight individually. The first flight would be Calgary to Tokyo (July 1) for CAD$934.91. The second flight is Tokyo to Manila (July 7) for CAD$342.85. The third flight is Manila to Calgary (July 17) for CAD$1002.70. The total price of this option is CAD$2,280.46.

calgary to tokyo OW
Calgary to Tokyo one way flight
tokyo to manila OW
Tokyo to Manila one way flight
manila to calgary OW
Manila to Calgary one way flight

Option 4: Call a travel agent

My family has a trusty travel agent but I usually just call her when I am in a special situation I cannot handle on my own, such as this one. To be honest, I mostly book my flight on my own but circumstances like this, I just can’t seem to figure out how to do it in the most cost-effective way. She just works her magic. Her best offer to me is CAD$1,799 for the itinerary: leave Calgary July 2, leave Tokyo July 7, and leave Manila July 17. The only difference for this option compared to the other four options is the departure date of July 2 from Calgary instead of July 1.

Option 5: Call an airline directly

My travel agent told me that to accommodate my request of having a few days of stopover in Tokyo, the airline that has the best deal is Air Canada. She also looked at Japan Airlines but said theirs is too expensive. Following her advice, I called Air Canada directly. Air Canada’s best offer to me is CAD$3,200 for the itinerary: leave Calgary July 1, leave Tokyo July 7, and leave Manila July 17.

Verdict: As you can see options 1, 2, and 3 are not very far off from each other with only a few dollar difference between them. However, the cheapest option is to book the flight offered to me by our travel agent (option 4). I don’t know how she found that deal but based on my research and comparing her offer to flights I have found online, hers is cheaper by approximately CAD$400. According to my travel agent, she can have me in Tokyo by 2 p.m. on July 3 while Option 1 will have me in Tokyo by 2 p.m. on July 2. If having that extra day in Tokyo is more important to me than saving dollars, then maybe Option 1 is the best choice (as long as I am willing to shell out CAD$400 more for an extra day in Tokyo). Let’s say I decide to spend CAD$400 more for an extra day in Tokyo, even if Option 2.b is cheaper than Option 1 (by approximately CAD$70), it is not worth it since what I save in money, I pay for it in travel time since I will arrive in Tokyo July 3 for option 2.b instead of July 2 for option 1. In addition to that, for option 2.b, I would have to leave Manila on July 16 instead of on July 17 as shown on option 1.

Do you know of a cheaper way for me to book my flight Calgary to Manila with four or five days stopover in Tokyo? If yes, please share it with me? You can comment below or if you want to keep it our little secret, you can e-mail me at

Also check out a fellow blogger’s “Ultimate Guide on How to Survive a Long Flight”



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  1. Oh, this is so useful. I’m trying to plot a long stop over in Kyoto before making my way to Manila… and hope to do the same thing (but to a different country) on the way back. I’m definitely going to give this a shop, thanks for sharing!

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