The whole trip took 10 days. We spent 4 days in NYC, then took a bus to Cleveland (12 hours by bus), spent a night there and went to Rock'n'Roll Hall of Fame. We left Cleveland that evening (rented a car there) and spent a night in a motel somewhere between Cleveland and Detroit (don't remember the name of the town). The next day we came to Detroit and visited Motown museum. Detroit is a really scary looking city, there are a lot of abandoned buildings and it really looks like an unpleasant and dangerous place. We decided not to stay there for the night and chose a motel somewhere on the way to Chicago instead. And the next day we were in Gary by noon. I thought we'd spend an hour or so there, but there was a lot to see so we spent there almost the whole day. And for the rest of our trip we were in Chicago (two days).