(Others will know better as I've only driven through a few times)
West Mi/Holland- Nice small downtown, quaint, lighthouses and rental cottages, a bit rural outside of that, may be busy during summer season.
Gary IN- Industrial, crime, stay away, same for South Side Chicago and Cleveland,
Chicago- The 94/90-55-290 freeway area is a log jam at rush hour and a chore to drive through. An hour of stress. Oak Park to the west has Frank Lloyd Wright houses but farther outside downtown. The North Shoreline I've never visited.
Look at crimes maps vs. the places of interest you'd like to visit.
Compare with prices.
