this post was submitted on 06 Sep 2025
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Chicago is a major democratic leaning city infamous for its association with lawlessness and organized crime. Reality is that Chicago cleaned up with the other cities but it maintains a rambunctious similar to LA and Philadelphia. But it's still got a local culture of early 20th century gangsters like Al Capone and other Italian Americans with submachine guns.
The entire great lakes region that includes Chicago had a pretty rough time from the 70s-00s, with other cities in it including Detroit, Cleveland, Buffalo, and Toronto as well as tiny hellholes of deindustrialization like Gary.
Chicago is also notably a very black city, especially by Midwestern standards. During the great migration (when a bunch of black people left the rural southern areas their ancestors had been enslaved in and went to urban areas largely in the north and west), Chicago was one of the major destinations as there was a lot of work that didn't involve farm labor.
So yeah mocking Chicago sometimes will have racist implications (though this applies to any great lakes city when compared to the overwhelmingly white rural and suburban Midwest).