The key to understanding Chicago is that it is a totally insular, isolated, politically homogenous, in-bred bubble. It is basically a city-state much in the same fashion as New York City. It is an independent realm with it’s own unique zeitgeist which so happens to be morally, politically, intellectually and criminally corrupt and beyond redemption.
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Really a pretty good description. If you think about it, North Korea is not that different. Except Trump can actually discuss policy with Kim Jong Un, not so much with our homegrown dictators.
Best plan is to avoid at all cost. Both places.