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Your Take on Convenience vs. Cost: How Do You Choose?

A few weeks ago we booked our tickets to Hawaii, where we will be spending our honeymoon, and we had a quick little $60 decision to make. On the way back, we have the option of two flights:

The two flights were similar otherwise (the first had one extra stop, but you never deplaned and second flight had a longer layover) so the difference was in just the flight time and departure times. The first flight was $60 more expensive but we were able to stay in Hawaii an additional hour and we arrived at home an hour earlier. So, which flight did we choose?

We chose the more expensive flight. This was probably one of the first times in which I’ve chosen convenience over cost when the two choices were so similar. In this particular case, there were reasons to pick the more expensive flight outside of the characteristics:

How do you go about deciding whether to take the cheaper option or the more convenient option?