The Chicago metro area, including its suburbs, in many ways resembles large cities in the Northeast along the Acela corridor more than it does other Midwestern large cities. It's a world city and has much more of the "new economy" for lack of a better term than other major Midwestern cities do. There is much more vibrancy and less industrial decline than you find in Cleveland, Detroit, Milwaukee, etc.
The new economy vs. old economy dichotomy explains a lot of the 2016 swings nationwide.
Even though every county in the Milwaukee Metropolitan area swung to Clinton.
Fair enough, I should have left Milwaukee off my list. Rest of my point still stands.