Hello from the Chicagoland area!
I've been putting together same trip the last few days. It's nice to see folks recomending the places I just booked- Yogi in Sioux Falls, SD for way there, Custer State Park (North Stockade Lake loop was recomended by a friend), and the KOA in Jackson, MN for a layover/laundry stop before our last State Park on way home. Anyone ever been to Pikes Peak State Park in IA?
We try to do 1 new Yogi a season with our 7yr old. Yogi and KOAs great for kids between State Park type campgrounds (plus you can get some laundry done).
A few coworkers mentioned Wall Drug. We might check that out. I'm also looking into Chuck wagon cookouts.
This will be our second season with our x23b. Can't wait!