Born in Chicago and raised in and lived in various burbs until moving to Michigan in '94. To me it's the finest big city in America, with Boston the number 2 and you can have all the others...especially New York.
Yes, it has crime problems. What big city doesn't? But it's mostly contained within various black/Hispanic neighborhoods, occasionally spills out to other areas like certain beaches, but the authorities generally shut that stuff off pretty quickly.
The Democrat machine government is as corrupt today as it has been over many decades now, same as other big cities, but the trash gets picked up, winter streets get plowed, the CTA is a good public transportation system, and residents are generally safe if they stay out of the aforementioned crime neighborhoods.
We visit the city so often the boss is twisting my arm to buy a condo downtown, to which I've put up only token resistance thus far and will likely fulfill her wish by this time next year. After all, the closer to my Cubbies and Wrigley Field in the summer the better.
If you haven't been to Chicago you're missing a lot.
