I like Chicago. I chose to move here. I did so because it is relatively liberal, its residents are generally friendly, the City has terrific arts and culture, is relatively affordable, and is built on a human scale.
However — and I think this is unfortunate — Chicago is best known for its dark side. There are a many reasons for this. Chicago is a very down-to-earth place. It doesn’t have a distinct, flamboyant style as Los Angeles and New York do. The City is an amalgam of distinct neighborhoods; these are individuated in a way that the City as a whole is not. Also, while Chicago’s arts and culture are robust, they are not usually locally distinct except, historically, in architecture and popular music.
Of course, the biggest reason is that Chicago is politically rotten. It exemplifies more than any other American city other than New Orleans one of H.L. Mencken’s innumerable great lines: that “every election is a sort of advance auction in stolen goods.”
As blogger jossip.com notes:
The reason Chicago politics is so corrupt is because, in modern American history, it’s never not been, which makes it very difficult to clean up. Especially because every politician who says they’re going to try and straighten Chicago out ends up lying and cheating worse than the pig who came before him.
Curiously, there’s relatively little effort to hide the filth. One feature of the City serves as a metaphor for this: alleys. Chicago is full of them; they run behind almost all residential streets.
Chicago doesn’t so much hide its dark side as compartmentalize itself. The nicer elements of the City are displayed most prominently, but the trash cans are always on view in the back.