The time I got 3 cents per Skymile and saved Christmas

That was exciting.

I've mentioned my upcoming flight in Alaska Airlines First Class to Hawaii to celebrate Christmas with my family (and earn Delta Platinum Medallion status). Well, Sunday's the big travel day, which means that my travel partner is flying tonight from her home base in the midwest out to New England so we could be on the same flights to Kauai. That was important to me because if there are any weather or mechanical delays along the way, I wanted to be able to troubleshoot the issues with her rather than leaving her stranded to negotiate rebookings, hotels, meal vouchers, and the rest of the hassles of winter travel on her own.

Unfortunately, when we booked the ticket a few months ago, it seemed like United's price and schedule worked best to get her out here. I say it "seemed" like it, because I failed to take into account the "United premium" of delays, missed connections, terrible customer service, and the overall disaster of an airline they represent.

With a delayed flight into Cleveland, there was no way my partner would make it into New England tonight. If she was rebooked onto a flight tomorrow, then we'd lose the Saturday buffer in case of additional weather problems. The only way she would get into New England tonight was on Delta:

That flight costs $1,219.60! Using Skymiles, on the other hand, I was able to book the outbound leg at the "Peak" (previously "high") level, and the inbound at the "Saver" (previously "low") level, for a total of 42,500 Skymiles and $10 in taxes and fees. That's a nominal value of 2.85 cents per Skymile.

Now, it's fair to point out that I wouldn't have actually paid $1,220 to rebook her onto Delta. Rather, I would have let United handle it, rebooking her onto flights tomorrow and causing me a huge amount of stress waiting to see whether she makes it in time.

That's the distinction I was driving at in this post back in April. While it's not fair to say that I used my miles to "save" $1,210, since I wouldn't have paid that much for this Delta ticket, it is fair to say that the 42,500 Skymiles I used, which cost me perhaps $243 to manufacture (earning 1.4 Skymiles per dollar, spending 0.8 cents per dollar), bought me something that's worth at least several times that much (including a ticket, my peace of mind, and a buffer day in between traveling), and in that sense I really did get an outsized return on my upfront investment.

Two Alternatives

There were two additional alternatives that were conceivable in this situation. First, I could have bought my partner the paid Delta ticket using my Barclaycard Arrival World MasterCard, and redeemed Arrival miles against the purchase. To earn 122,000 Arrival miles, I'd need to spend about $61,000 on the card, which would cost me perhaps $488. That would be slightly more expensive than the Skymiles option, but it would leave me with the 42,500 Skymiles, which is about a third of the new cost of a transatlantic BusinessElite ticket.

Alternatively, and I might have tried this if I were flying with my partner, I could have asked United to rebook me on the Delta flight tonight, instead of paying for a hotel in Madison or Cleveland. Airlines are sometimes willing to do this, although it will depend largely on the agent you're dealing with and how hard you're willing to push. Besides the fact that I didn't want to put my partner on the spot to negotiate her rebooking, the real obstacle to this approach is the agonizing slowness of United customer service agents. If she waited in line to speak to the customer service representative, she would have missed not only the United flight to Cleveland, but probably the Delta flight to Detroit as well. I'd rather go online, book a ticket, and have her walk over to her new gate.

Plus, this way I scored huge brownie points, just in time for the holidays.