[notanlines]

Mike, you can ignore any grief towing around Cleveland. You won't really come close enough to have any problems unless you just happen to cruise by on Friday at 4:00.
We have towed through and around Chicago a number of different ways. None seem to work very well. Labman's two cents is probably as good as any.
Once you gain access to I-90 out of Minnesota you will be limited to very little in the way of scenery/hot spots along the way. Mitchell, SD corn palace, Wall Drug/Badlands NP, SD and then your final destination; Rapid City.
Rapid City area is a great place to visit. You can probably safely camp up towards the end of October, but not into November without freezing precautions.