When it’s the wrong time to buy the cheapest flight

Note: I’m currently traveling in Asia and will have limited access to the internet. Replies to comments and emails will be delayed.

Who doesn’t love a bargain? Finding a great deal on flights, whether by cash or points, is always a boon for travelers in this hobby. But, is there ever a wrong time to book the cheapest flight?

Last Leg Home from Japan

For our current trip to Japan, my son and his friend are flying from Tokyo to San Francisco on miles. I kept checking to see if I could find nonstop flights from Tokyo all the way to Dallas, but no dice. So, we’re stuck getting flights from San Francisco to Dallas for the last leg of a long trip.

Of course, I wanted to use miles OR find a cheap cash flight. I was happy to see that there was a nonstop flight between SFO and DFW for just $62:

I know that we’d have to add luggage fees on top of that fare, but still, it’s a great price.

Now the younger me would have booked that flight with no issues. But the current me had hesitations. This is a redeye flight on the tail end of a few weeks in Japan. Their flight from Tokyo lands in the morning, so they would have a very long layover. They will likely be very tired and just feel like getting home ASAP. That’s how I feel at the end of every international trip.

So instead, I used Alaska miles to book them nonstop flights home at a more reasonable hour. You’re welcome, boys.

Do you always book the cheapest bargain flight? Or, does airline or flight time play into your decision?