nearly all of Illinois in 24 hours with fuel costs in the $180 range.

how did you figure that? It's about 1400 miles from Chicago. Let's assume the car gets about 20 mpg and assuming that gasoline is ~$4 per gallon, it will be about $280 one way just for gas.

1440 miles @ 60mph @ 32 mpg = 45 gallons each way. My Honda Civic always does better than that. 45 gallons at $4 = $180.
For more than 2 people in a car, driving costs are less than the same number of people on a train.

Folks give it up. If not a troll==good post, you have to say. It isn't real.
Illinois=far north
beach=far south--AND warm
Not happening=true

Allegiant Airlines has incredible fares from smaller one off cities to Florida and Arizona.

As others have mentioned - I think a warm-weather destination is going to be out of reach, given that you don't want to spend a lot of time driving and train/plane fares will likely bust your budget. I agree with suze. Forget about warm and think cozy instead, like a lodge with a fireplace, etc.

The problem here lies w/teh 'warm weather requirement' coupled w/major Holidays. One or the other (or both) need to be reconsidered for the chosen price point...