Chicago to Charleston
 

My husband and I, in our 60s, are traveling from Chicago to Charleston this summer? Where do you recommend we stop?

Depends on how you go. I would go south from Chicago to Indy over to Dayton. Take Route 35 across southern Ohio (beautiful uncrowded road throuh beautiful countryside). You want to get to i77. Take it south through Charlotte and Columbia to I26 to Charleston.

Or Indy to Cincinnati to I75 south to Knoxville. I40 to I26 at Asheville and south to Charleston from there. You might like to stop in Asheville.

London Kentucky just off I-75. If you wanted to take a detour south of London, try US25E and go through the Cumberland Gap at the west tip of Virginia.

Thanks for your suggestions! What do you recommend to see in Charleston? It will be summer and I'm guessing very hot.

There are a jillion threads about Charleston--what to see, where to eat. Take a look

Yes, type Charleston into the search box at the top of the page.
If it is too hot, head west to the mountains.

I don't know how many days you want to spend getting to Charleston but if say, only two, I would try to get to Knoxville at least. It's another 7 hours to Charleston I think.
But for a nice "road trip", you could go to Asheville and spend a couple of days and then on to Charleston. Lots to do both places.