Out of all of the cities you've mentioned the only one you should checkout is Toronto,
Milwaukee has beer? Yay but Canada has much better stronger beer, Indianapolis sucks, Cleveland sucks, Detroit does have some cool stuff to see and do but I wouldn't waste a drive to Cleveland or Milwaukee or Indianapolis.
Chicago is cool has a cool music scene and plenty of great restaurants.
A few cool things to do in Michigan
Big Bear Sand Dunes
Manitou Island (great for camping 10-15 miles out from mainland)
Mackinaw Island
Traverse City Cherry Blossom Festival
Tipup Town Winter Ice Festival in Houghton Lake
If you are into hunting you will be a happy camper.
Also don't forget to pack your prozac.