Like most things it depends. Destination, what flights are available, time of the year, condition of the highways, what I need to bring with me, length of drive, planned activities when I'm there, whether I need a car at my destination, etc.

My home town is a 7 and a half hour drive, 5 hours doorway to doorway if I fly. The few available flights are inconveniently timed so I drive unless the weather is expected to be bad. Meanwhile, NYC is a similar driving distance but there are many flight options, I don't need a car while there so it wouldn't occur to me to drive.