Playing by the rules: taking advantage of two current promotions

Much of what glamour there is in travel hacking revolves around finding the play in the joints of rewards ecosystems, for the same reason “Ocean’s 11” was about robbing a casino, not staring dead-eyed at a slot machine for 20 hours straight. That’s why I rarely pay attention to the deluge of sales and promotions that are written up in the same pasted-from-the-press-release terms on sites sponsored by credit card companies and reliant on good relationships with loyalty programs.

So I was surprised to find myself taking advantage of not one, but two promotions in a single week to book two trips that offered me satisfying value for points balances that had grown too large and that I had been sitting on for too long.

When the travel hacking community had more diverse and interesting voices, a frequent argument was over how to value redemptions: should you claim the retail value of the actual flights you take and the hotels you stay in, or use a kind of “if-not” valuation using the price of the flights and hotels you’d otherwise pay for in a world without travel hacking, or even the out-of-pocket expenses you incurred earning your miles and points (while this last can be an interesting exercise, I don’t know anyone who actually uses it since it requires meticulously tracking the cost of acquisition of every mile and point you redeem).

In this post I’ll take a middle road and give the retail price of the seats I would have paid for on the flights I actually did end up booking.

Air Canada transfer bonus from Ultimate Rewards

My partner, who works in the real world, was anxious to take a long vacation this summer, and I was anxious to oblige her. Due to scheduling uncertainty, it was only at the beginning of June that I started looking for options to Europe later this month, and naturally, award availability had grown pretty limited.

Spinning around my digital globe, I proposed Andorra, the microstate nestled in the Pyranees between France and Spain. After a few hours of searching, I found that the two easiest routes (Andorra not having an airport of its own) were to take a long bus ride from Barcelona, or a train followed by a much shorter bus ride from Toulouse, France.

Favoring as little time spent on a bus as possible, I found award availability to Toulouse on Air Canada, with a single connection in Montreal. When I explained this option, my partner sensibly replied, “or we could just go to Montreal.” This suggestion was so obviously superior that I scrapped the Andorra idea completely.

There was award space every day on Air Canada using their own Aeroplan miles, which conveniently is a transfer partner of Ultimate Rewards, where in turn I’ve been sitting on a balance far larger than I’m usually comfortable with and no other obvious upcoming uses. When I logged in, I was delighted to see that through July 17, 2025, I’d receive a 20% bonus on transfers to Aeroplan (there’s also a 25% transfer bonus to Virgin Atlantic through June 15, 2025). For those doing the math at home, that works out to a roughly 17% discount on Aeroplan awards.

I’d never booked an Aeroplan award before, so had to figure out the curious 5-tier redemption system, with “Standard,” “Flex,” and “Latitude” (refundable) options in economy and “Lowest” and “Flexible” options in business. It turned out that the “Lowest” business redemption was cheaper than the “Flex” option I would choose in economy, so I transferred 174,000 Ultimate Rewards points and received 208,800 miles in my Aeroplan account. The transfer processed instantly, and I booked the award for 208,600 miles and $230.90 (315.35 Canadian).

The cash fare for the two economy tickets I would have booked on the same flight is $2022.28, which works out to a redemption value of 1.03 cents per Ultimate Rewards point after deducting the $230.90 in taxes and fees. Since Ultimate Rewards points are redeemable for cash at 1 cent each, that makes this a classic example of “paying for coach but flying in business.” Business class on my flights is now sold out, so it’s unavailable at any price, but the closest equivalent retails for $3208.76, or 1.7 cents per Ultimate Rewards point.

Alaska partner award sale

Alaska Airlines Mileage Plan miles are incredibly valuable for flying on short-haul American Airlines flights, but one reason they’re so valuable is that you don’t need very many of them: even around the holidays I find essentially unlimited award space at 4,500 miles in economy and 9,000 miles in (domestic) first class. Consequently, I passively accumulated Mileage Plan miles far faster than I redeem them, and ended up with a massive balance I’m constantly anxious to find a use for.

As I gather is common in the white collar world these days, we also have a work-imposed week off in August I needed to plan for, so I was delighted to see Alaska Airlines announce an award sale to six destinations: Bangkok, Buenos Aires, Lisbon, Monterrey (Mexico), Tbilisi, and Naples. Alaska does not, in fact, fly to any of these destinations except Monterrey, so in practice this a sale on the seats on their airline partners.

The sale is applicable to economy and premium economy cabins, but not business or first class, and tickets have to be booked by June 30, 2025, for travel between August 1 and November 15, 2025.

While I’ve visited Naples a few times on long trips through Italy, I’ve only scratched the surface of the surrounding areas, and the idea met with instant approval. Award space was wide open when I checked shortly after the promotion went live (it’s since thinned out a little), so I booked seats in premium economy for 100,000 Mileage Plan miles and $165.22 in taxes and fees.

Economy seats on the exact flights we’re taking retail for $1939.82, resulting in a redemption value of 1.78 cents per Mileage Plan mile. The premium economy seats we’ll actually fly in cost $3307.82, for a redemption value of 3.14 cents per mile.

Conclusion

First and foremost I want to point out that these promotions are still going on, so if you foresee any Aeroplan redemptions, this is a great time to transfer Ultimate Rewards points over, and if you’re planning a late summer or fall trip to one of Alaska Airlines’ discounted award destinations, certainly book (or rebook!) your flights to take advantage of these potentially steep discounts.

But there are a few other points worth highlighting in this context.

There is no alternative to actually redeeming your miles and points for keeping yourself intellectually and financially honest. This is different from omnipresent concerns about the “devaluation” of miles and points currencies; it’s about properly valuing them at all, and deciding whether you’re earning the currencies that you personally get the most value from. It’s all well, good, and profitable for affiliate bloggers to spout fantastical valuations of every loyalty currency under the sun, but the only value that matters is the value you actually get for the trips you actually want to take.

Finally, there’s a big difference between choosing between classes of service, or between luxury and no-frills carriers, or between destinations (shall we summer in Montreal or Andorra this year?), and choosing between traveling or not traveling.

Years ago I recall a Netflix executive was quoted somewhere saying “our biggest competitor is sleep.” Speaking for myself, travel hacking is only partly and occasionally about splurging on business class when economy would serve, or staying at the Waldorf Astoria when there’s a Hilton Garden Inn next door. Travel hacking for me is about making travel possible in the first place.

Outside of business travel, most people I know fly internationally at most once a year, and only a few times more than that domestically, and if I had to pay out of pocket for flights and hotels, I’d do exactly the same. Travel hacking lets me travel very literally outside my means: not because of the threadcount of the hotel sheets, but because I get to sleep in hotels at all.