I am planning a trip from my new workplace of Johnson City, Tennessee, to my family’s stomping grounds near Chicago, Illinois, early in the summer. Since I’ve done this trip a few times, I’ve already driven the most obvious routes, as you can see in this map:

What I would like is any advice you see fit to give for a routing and activities, both roadgeeky and not, about a new way to get back to Chicago. I am not averse to going a fair a bit out of my way and seeing some new stuff. The trip is normally about 700 miles, and so anything less than 1,000 would work nicely. Do you have any ideas about what I could do? Should I head east into West Virginia and Ohio before heading west, or should I check out the new bit of I-69 in southwest Indiana? Are there any good routes to clinch?
I’m hoping to make this a two-day trip, maybe staying in a hotel for the night or perhaps hauling out my tent. So, information on good places to stay would also be more than welcome.