Brutal Realties: Collecting Travel Rewards in 2023

by Robert McGarvey

It is time to play hard. Winning at travel rewards requires cunning, guile and, well, a determination to win.

I just won but I am still amazed at what I did to pull this off. It wasn’t hard – quite the contrary – but it seemed so unlike me.

Regular readers will recall that a few months ago I got a barebones Southwest Air credit card via Chase – $69 fee per year. It delivers minimal perks. But – crucially – it offered 50,000 SWA miles when spending $1000 in the first couple months of the card.

I had a trip for two to Dallas on my calendar, just a handful of miles in my Southwest account and not much more at American, and, no, I am not flying Frontier or similar discounters because I’m not. So I was looking at around $700+ out of pocket for air for a short trip to Dallas from Phoenix for two.

I did the math and it seemed to me I was out $69 if I get the card plus, say, $20 in lost Amex miles value for the $1000 spent to collect 50,000 miles – but I would collect $700 in value with the two free tix. Case closed, I got the card, and yesterday I booked the flights for about 52,000 miles (I had the extras in the account from a years ago flight on SWA) plus $11.20.

Add it up and I’m out about $100…but I saved $600 net.

Probably I will cancel the SWA card when it comes up for renewal.

It took me a few seconds to apply for the card, it will take about the same to cancel it.

And then I’ll move on to another card with a sign up bonus. Probably Alaska Air because it has rich payoffs (even if I don’t see me flying it but the transfer partners are plentiful – oneworld members plus a handful more including Aer Lingus).

What is so strange about all this is that, just a few years ago, I looked with pity upon friends who were deeply immersed in playing the credit card and mileage games. It seemed like so much effort. And yet here I am.

What’s changed? Really, it all changed when the airlines ditched their awards charts and instituted “dynamic pricing” aka what the market will bear and, suddenly, roundtrip shoulder flights to Europe in Economy Plus (not business class) cost over100,000 SkyMiles on Delta and who would have thought the cost could hit that mark?

I had always thought miles were a kind of adult Monopoly money and, boy, did that become plainly fact in the era of dynamic rewards pricing where airlines seem to work on the belief that there always is a greater fool so let’s push the cost higher and someone with a bunch of miles who believes they were “free” will plunk them down.

That’s not me. Miles I earned flying are miles I feel in my body. I worked for them, I earned them.

Now, miles I get for playing a sign up hustle are different. They are free or close to it.

And, really, the only way to play the miles game now is hustling for sign up bonuses. Earn ’em, spend ’em, move on.