I spent a fair amount of time in Chicago and a few burbs in the 90’s. Loved it, actually. Architect’s town, so many stunning buildings, even entire older neighborhoods in the prairie style, long and low, deep eaves. Foodie town too, from excellent inexpensive diner food in huge portions all the way up the line, whatever you wanted. But, even then it was like an island less than a mile wide that went feral the further south you got, there was a line you just didn’t cross and if you did, you ran stoplights to avoid getting shot. Certain areas it was like that going inland away from Lake Michigan although the corridor out to O’Hare was very thoroughly policed. Back then, serious crime up north along Michigan Ave was not tolerated. The tourist areas were kept largely free of criminal elements. They knew where their bread was buttered. Sounds as if that’s no longer true, and if so it’s a pity, that Manhattanesque downtown but bright, clean and pretty. What a waste, and for what? Pandering to the lowest common denominator.
Yeah the Magnificent Mile up to Evanston and beyond was lovely. But west of that things became steadily more dreary. I have depressing memories of broad avenues in westside Chicago that led to nowhere, with few signs of economic viability. And everything south of the Loop was very dangerous.