I am planning a trip from Summit , NJ to Chicago on July 12th. I have booked 13th ,14th and 15th for local downtown Chicago. I am open thereafter. I have thought of making a trip to Pontiac,IL, to check on Route 66. On my way back,I want to stop 2 days in Detroit ,MI and Cleveland,OH.I hope to back by the next weekend., making it about 10 days round trip.
I need advice as to where we can break for the night on way to Chicago and what is the best route we should take in and out and is there and interesting place we can add to the trip.