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Round trip from Chicago

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Greetings,
a friend of mine and I are planning our another trip to the United States. This time we've picked Chicago as a starting point.
So, we have some 16-17 days from mid-October till early November 2014.
We'd like to spend about 3-4 days in Chicago and make a trip by rented car to the neighboring cities/states. At the point we've worked out the following preliminary itinerary:
1 day - from Chicago to Cleveland
2 day - Cleveland. By the way, will the Rock'n'roll hall of Fame be interesting for those who are not big fans of clasic rock of 60-70's but are buffs of heavy music of 80's?
3 day - from Cleveland to Buffalo
4 day - hotel in Buffalo, trip from Buffalo to Niagara Falls and back
5 day - from Buffalo to Pittsburgh
6 day - from Pittsburgh to Columbus
7 day - Columbus
8 day - from Columbus to Indianapolis via Cincinnati(short tour through the city)
9 day - Indianapolis
10 day - from Indianapolis to Saint Louis
11 day - St. Louis
12 day - from St. Louis back to Chicago
13, 14, 15, 16 days - Chicago
The itinerary, as I said, is pretty raw and honestly I'm not sure it's the best possible one at all. We've never been midwest before and have very vague idea of the area. Suppose the nature in October must be great over there, right?
I (unlike my friend) have some qualms about St. Louis and Pittsburgh.. Maybe we should better visit Detroit instead? On the flip side I hear Detroit has fallen into decay recently and become not too safe city for tourists at all. True?
Also I've heard that Milwaukee offers the best beer in the USA. Is it worthwhile driving there almost 100 miles from Chicago to spend a night?
So, all in all, we still have more questions than answers concerning the journey)
The principal goal is to see as much of everything as possible and snag at least a couple of the NHL games)))
I'll appreciate a lot your advice/critics/suggestions on the subject.
Look forward to your feedback. Thank you.
P.S. Or maybe we better forget about Niagara Falls and head to Minnesota right from Chicago? (just occur to me looking at the map :))

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