Theil - yes, avoid Chicago. We rolled down 30 after skirting the Chicago area and picked up 33 out of Fort Wayne. It was a nice tow after the wind died down. Several stops were in the consider plan, but they seemed lacking at first look. The end result was that we pulled into the Airstream employee parking lot at about 1:00am and called it good for the night. It was a Saturday, and that is a bit different than norm as we expected no company in the am.
Good luck with your plan. Might give Jefferson Township Community Park a look. It's a half dozen sites, but might be a bust as it is close to a rail spur.
Sometimes best is out of the way. Sometimes it's at the local Walmart.
Pat
Edit - we did pick up some character from a road gater, so take care.