A few years ago, nudged along by a handful of social media accounts, I rolled up my sleeves and marched confidently into the world of credit card points and airline miles.
In the U.S., credit card perks can be absurdly generous. One of the biggest draws is the sign-up bonus: open a new card, meet the spending requirement, and receive a large pile of rewards. Often these rewards do not arrive as cash, but as points in some credit card company’s system. Depending on how you use them, the value you get out of those points can vary wildly.
The most outrageous redemption, at least in theory, is to transfer those points to an airline and book long-haul business class. Cash prices for business class tickets are often shocking, partly because many of the people sitting up front are traveling on company money, with large corporations buying the tickets for executives and not worrying too much about the cost. But if you can find award availability, the miles price can work out to be cheaper than flying economy.
How could I possibly ignore such a magnificent free lunch?
So I studied redemption strategies, read up on airline partners, and even paid cash to buy miles directly from airlines. In my head, I was always one clever booking away from a glorious win.
My actual results: I have never successfully redeemed a single business class ticket between the U.S. and China.
There were several reasons.
- There simply are not that many flights from Chicago to Asia to begin with.
- My family is not small. Even if I found one award seat, what was I supposed to do—send one person off in business class while everyone else sat elsewhere?
- School breaks always fall during peak travel season. Expecting a bargain award seat to drop from the sky during those windows is basically fantasy.
- And finally, U.S.–China business class awards are not just being watched by ordinary people like me. They are also targeted by all kinds of middlemen, ticket brokers, and professional award hunters who are much better at grabbing seats the moment they appear.
The miles I had accumulated became increasingly awkward to use. Some were getting close to expiration. In the end, I often had to burn them on random, mediocre-value tickets just so they would not go to waste.
After all that maneuvering, I would not say the miles game made me lose money. But I also never extracted the huge upside I had imagined. My conclusion is that this game is really only worth playing seriously if all of the following apply:
- You do not have kids, and you enjoy spontaneous travel.
- You live on the East Coast or West Coast, where there are far more long-haul direct flights.
- You genuinely enjoy bargain hunting, and “finding an award ticket” is part of the fun for you.
- You have the time and energy to monitor award availability the way some people watch the stock market.
At this point, I am not even sure I still have much of number three left in me. Once I use up the miles I currently have, I may take a break, reset my mindset—and then maybe come back for revenge.