Illinois is a big state... where are you planning to start? Quad Cities per your sig?
Whenever we leave Illinois, our goal is to be out of the state in one day...
Our preferred routing to FL is I-57 to I-24 to I-75. By not stopping anywhere in Illinois in December, that means pretty much getting away from exposure to freezing temps.
6 hours gets us to Paducah, 8 gets us to Nashville, 10 gets us to Chattanooga.
Never stopped in Paducah (not even for fuel)...
Nashville has good music history, great food, and lots of places where you can get live music with food... Bringing a 30' trailer into those areas downtown? Not so much fun, but if you're going to overnight in a campground, you've got options to drop and run for a couple hours of fun or you can call an Uber...
Chattanooga is two hours further down the line, and more or less the halfway point, so it's a more logical stop for us. Lot of Civil War related sites in that area to visit either as a slow drive-thru or by dropping the trailer and being tourists for a day.
Can't speak to much of anything south of there -- we're either two day drivers or round-the-clock-non-stop when we head to Florida just because I still work and rarely have more than 8 days off at a time.
Hopefully someone else has some ideas on that I-75 corridor.