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Let’s be real: we have all made some poor points redemptions at one point or another. On the scale of bad redemptions, I think my worst is paying 34,000 Aeroplan points for a Toronto–Ottawa economy flight. I love optimizing and maximizing my points, so I’m usually trying to redeem for premium cabins at saver prices. In this case, a series of events led me to redeem Flying Blue points for an international WestJet Economy flight.
What I Booked
To get this out of the way: I redeemed 54,500 Flying Blue miles + $35.80 CAD for Tokyo (NRT)–Calgary–Ottawa on WestJet in economy for my younger brother. To be frank, I don’t think it’s objectively that bad, but it certainly hurt me inside to spend so many points on economy and especially on WestJet.
In comparison, I booked Tokyo–Seattle on ANA in business class for 55,000 Aeroplan points a week earlier, so my partner could return to the United States. To keep the whole redemption satisfying, I booked the final leg, Seattle–Miami, on American Airlines economy for just 6,000 AAdvantage miles.
ANA 787-9 business class
The Issues: March Break in Japan
To set the context, my younger brother has been wanting to visit Japan. As a high school student, his main breaks are summer, Christmas, and March break. March break is the natural time to visit, as we like to spend Christmas at home, and summer in Tokyo is sweltering. Since high school began, he has been less willing to miss school days (completely understandable).
So here’s the first issue: he has exactly 1 week (+2 weekends), so we want to maximize time on the ground by leaving Ottawa on Friday and returning home on the Sunday after. The second issue was that he informed me he didn’t want to visit in March, as it’s too short, and he wants to wait until he has more time off, maybe in a few years when he’s at university.
Fair enough, except in May, he decided he wanted to visit for March Break after all and asked me if it was still possible. Not wanting to disappoint, I said I’d figure something out. The final issue (caused by me this time) is that I would already be in Asia, so my 15-year-old brother would need to fly solo round-trip.
For Japan, I’ll do (nearly) anything…
My rookie mistake was not booking flights one year out. Even though he said he didn’t want to go, I should’ve taken a page out of PMB writer Sash’s book and booked speculative flights anyway. Japan’s two major airlines, ANA and Japan Airlines, both reliably release space about one year out, though often not until close to departure. Trying to find business class award space for March 2026, starting in May 2025, is an uphill battle, especially with no date flexibility.
The Outbound Flights
Since virtually nothing was available, I set a bunch of Seats.aero alerts and basically hoped for the best. In October 2025, WestJet had an excellent cash price for Ottawa–Calgary–Tokyo one-way in business class for $1,354.80 CAD. Not low enough to be a mistake fare, but for business class on my ideal date? I booked it immediately (only available via BudgetAir).
WestJet 787 business class
The Return Flights
The return proved more complicated. Knowing the release patterns, I planned to book something close in. Given the restrictions, I was happy to take economy if it was available at saver pricing. I found Osaka–Hong Kong–Toronto on Cathay Pacific in economy for 38,000 Asia Miles and transferred Amex MR points. Rookie mistake number two — the transfer took about five days, and the award space disappeared. Asia Miles allows three-day holds, but it requires a phone call, which I neglected to make.
Saver Space Available, But…
Over the following months, I received several useful Seats.aero alerts for the ideal return date. These included Hawaiian Airlines business class from Tokyo to Seattle, ANA business class from Tokyo to Washington, D.C., and AA economy from Tokyo to New York JFK. However, arranging positioning flights for my brother turned out to be harder than expected. He couldn’t check into a hotel during an overnight layover, and switching airports alone wasn’t an option. Positioning from Seattle to Ottawa was also expensive, with only poorly timed flights available.
I could’ve booked Tokyo-Seattle on Hawaiian Airlines business class, but…
Given these additional restrictions, I decided I wanted to secure flights immediately and not take my chances with last minute award space. After way too many hours, I decided on WestJet for the return as well: Tokyo–Calgary–Ottawa. It fulfilled multiple conditions:
- Maximize time on the ground
- Tokyo to Ottawa with only one reasonably timed layover
- All on the same ticket, so there’s ticket protection in case of IRROPs
- The international flight goes straight to Canada without connecting through a third country
The last one isn’t a must, but a “good to have” for my brother travelling alone. Most importantly, it cost 54,500 Flying Blue miles, which I had acquired through a 20% Amex US MR bonus (aka I spent 46,000 MR), which helped me feel a bit better about the situation. Taxes and fees were also reasonable at just $35.80 CAD. Compared to Aeroplan charging 150,000+ points one-way in economy class…
WestJet 787 economy class
I continue to have Seats.aero alerts set and will change if something better opens up, but I’m 90%+ certain he’ll fly this. One option is EVA Air last-minute award space through Taipei, but again, that would require him to position from Tokyo to Taipei, then again from EVA’s North America port (Toronto or Chicago, if I’m lucky) to Ottawa.
Takeaway
This ended up being one of the least satisfying redemptions I’ve made in years: 54,500 Flying Blue miles for a WestJet economy flight from Tokyo to Ottawa via Calgary. As icing on the cake, I also paid cash for business class on the outbound flight (albeit at a reasonable price).
But the experience reinforces an important lesson about award travel. When you’re not planning sufficiently in advance, have fixed travel dates, and can’t be flexible with routing, premium cabin saver space becomes extremely difficult to find. Even seasoned points collectors sometimes have to settle for an imperfect redemption to make the trip happen.
