No, buying miles and points still (usually) doesn't make sense

On Sunday I described a mistake I made when making an upcoming Marriott reservation: since Marriott allows you to purchase points for 1.25 cents each, if a Marriott redemption makes sense on the merits (I wanted to stay at the airport the night before my departure) then you should buy any points you need. Instead, I transferred super-valuable flexible Chase Ultimate Rewards points from my Sapphire Preferred account, even though those points are worth at least 1.25 cents each when used to purchase paid airline tickets through the Ultimate Rewards portal.

That reminded me of an e-mail I received recently from reader Kimberly in San Diego. She asked:

When I checked in for a united flight from San Diego to Chicago they asked if I want to get double miles (over 1700 extra) for around $60 I think. The ticket was $400. Should I do it?

This is the kind of split-second decision that frequent flyer programs love forcing their customers to make. After all, checking in at the airport you might not have any idea whether this is a once-in-a-lifetime opportunity to stock up on points, or even whether it's a better deal than buying points online at That's one reason why you should always have a general idea of what a mile or point is worth to you.

Now, some travel hackers take this to extremes and try to establish specific prices they're willing to buy points at and specific values they're willing to redeem points at. Those travel hackers also accumulate vast quantities of miles and points because they're always waiting for the perfect redemption. 

My approach is slightly different, and it works better for my lifestyle: I'm always eager to redeem my miles and points instead of spending cash, but I also only acquire them at the lowest cost possible: that's why I have a single-minded focus on my cost per point. For example, when the no-fee Hilton American Express card gave 6 Hilton HHonors points per dollar spent at drug stores, it was possible to earn HHonors points at a cost of 0.13 cents each. For me, that makes it academic whether I'm redeeming my HHonors points for 0.55 cents each or 0.8 cents each: either way I'm beating the house every time.

That brings me back to Kimberly's question: should she buy 1,700 United MileagePlus miles for $60 when she checks into her Chicago flight? For me there are three numbers that make this decision easy:

  • 25,000: the number of MileagePlus miles required for a domestic round-trip award ticket;
  • 60,000: the number required for an economy transatlantic award ticket;
  • 100,000: the number required for a business class transatlantic award ticket. 

Those are the three awards I redeem my MileagePlus miles for most frequently. And purchasing United miles for 3.5 cents each would value those tickets at $875, $2,100, and $3,500, respectively.  Since I know I would never spend that much money on one of these tickets, I know that I should pass on the offer to buy miles.