We drove from Chicago this last Thanksgiving week to Vero. This was our first time driving, and as someone else mentioned I was leary of flying so we cancelled our air and drove instead. It wasn't half as bad as I had imagined

We used our minivan which gave myself, dh, ds (14), dd (13) and dd (5) enough room to be comfortable. My husband and I bought some new DVD's for the kids to watch on the trip down and it worked out great. He figured out how to hook up three sets of headphones, each with individual knobs for volume control to his laptop. The kids also brought lots of things to keep them occupied, such as books, drawing ativities, game boy, CD player. I thought we were really indulging our kids with the laptop and DVD's until my husband noticed a SUV next to us with three seperate television sets in the back of the seats, all showing different movies.
We winged it in regards to getting a room. The actual driving time was around 22 hours for us. We left around 5 p.m. on a Thursday drove till around 2 am, got a room until 7 am, hit the road again until 9ish, where we got a room right out of Ocala. Got up the next morning, met my grandma who lives in Ocala for bfast and headed off to Vero, pulling in around 1:00. The trip home, we left early Sat morning, drove until about 9, I think we were in TN, but could be wrong, got a room somewhere off the interstate, got up early the next morning and made it home to the far NW burbs of Chicago by dinnertime.
I am not too keen on driving again, but would "consider" it, lol.
Good luck, and have fun,
Kelly