Not crazy at all. We drive just about everywhere because the price to fly with a family of 6 is INSANE...as a matter of fact I *just* priced United and for our family it would be over $5,000 to fly.
I don't care what the cost of gas is, even taking that into consideration, hotel costs & food it is not anywhere NEAR $5,000....it is a trade-off with time though.
Well if we're playing "who can find the most expensive flight" I have the number for a good charter service here. Figure about $12,000 for a modest Citation Bravo to take you there quite comfy.
Southwest says they'll do six RT tickets non-stop MDW to MCO for $1,764 any day in July 2011. 2.5 hours start to finish. Still more expensive than driving...but not unreasonable in my book. Prices might even come down between now and then.