My Track Record with Booking Last-minute “Better” Award Flights

Unrelated news update: As of 5 a.m. ET this morning, Global Entry is reopening. Yay!

The great thing about booking flights with miles and points is that you can potentially change your plans without losing all of your money. Many airlines let you change/cancel award flights for free, while some charge a cancellation/change fee. But still, usually that fee is better than losing the entire fare.

I try to book award flights as soon as airlines release the flights, usually 11-12 months ahead of time. When I find something that works, I book it before the award availability is gone. I don’t always get the top cabin or routing, but I book something that I can live with, knowing that potentially I can change my trip if I find something better closer to my trip time.

My Track Record with Booking Last-minute “Better” Award Flights

Well, I’m not going to sugar coat this: My track record is bad. Despite setting price alerts and constantly searching for better routing or an upgraded cabin, I’ve never had luck with last-minute award bookings.

For example, when my family went to Japan last year, I had to book my son and his friend on Economy. Unfortunately, even though I kept searching, no Premium Economy award seats opened up for our dates. Similarly, my daughter and I flew home from Shanghai in Premium Economy. I would have loved to fly home in Business class, but nothing ever opened up.

In a few days, my family is traveling to the Caribbean for spring break. For our flights home, we actually have two stopovers: an overnight in Miami, followed by a short layover in Houston before landing at DFW. I had hoped we could find a nonstop flight from Miami to DFW eventually, whether with miles or a cheap cash fare. Alas, that didn’t happen. Both cash and miles prices for a nonstop flight over spring break are ridiculously expensive. Even though I’m now dreading two layovers, it is what it is.

In a few months, my daughter and I are traveling to Asia again. Our return flights are a bit cumbersome right now: Krabi to Bangkok to Hong Kong to Seattle to DFW. The long flight is in Premium Economy. I’d love to find a more direct route or  an upgraded award flight in Business class. But, I’m not counting on it.

Have you had luck finding last-minute better award flights? I’d love to hear your experiences.