Flying my family out visit my inlaws over christmas this year would cost $5000. I'd like to avoid the time driving, and if it was me I probably would, but the additional costs of the whole family make it not affordable. Car maintenance doesn't cost that much. While flying is a day faster in the best case, I've been stuck in a city I didn't want to be at because weather caused a missed connection (the airline wouldn't have 5 empty seats on a plane for a week - lots of last minute headache trying to find a different option to get to the funeral on time - driving puts me much more in control of this)

When I'm at work my company paid for flights, but even then many will tell you if it is only 12 hours to drive, just rent a car: flying is a headache and doesn't really save enough time to be worth it. (if you are going to/from a major hub then flying is great, but we often go between minor cities, which means several hours at various airports)

Ouch, 5,000$ for a family of 5 to travel ~1,000 miles x 2 with lots of notice seems crazy to me, but I live near a major airport.

So for me it’s generally fly to whatever the closest major airport is then rent a car and drive the last leg. That shaves most of the driving and avoids layovers etc while adding 3-4 hours for the flight + airport.

I can see you driving up to say 15h, but even then for a 20+ hour drive you might as well drive to a major airport fly and then drive the last leg.