Re: Winter Roadtrip Chicago..Stuck!!
If you're worried about snow, what about heading south? Looks like Nashville is less than 500 miles from Chicago (according to Mapquest). I don't know that part of the country well at all, but I bet with a little research you could find some fun things to see on a swing through the Midwest/Southeast.
Or you could head east to Washington D.C. (~700 miles), passing through places like Gettysburg and Baltimore. It would be a long haul, but you'd be on major roads at all times so hopefully your itinerary wouldn't be as vulnerable to bad weather. (You could ditch the car and hop on public transportation while you're actually in DC too.)
Hope that helps a little! Let us know what you decide.
"I haven't been everywhere yet, but it's on my list." -- Susan Sontag