Earlier quoted context omitted.
I live in Chicago so I know that feeling. We’ve been on the cusp of dying since the 1970s.
Chicago, while not dead, is a fraction of what it used to be. While it used to be at the vanguard of US cities, when is the last time you’ve heard it mentioned in national news in a good way? Not all cities end up like Detroit. Some just fade into irrelevance.
Incidentally, Zillow has Chicago and the surrounding metro area posting the highest growth in home value (source: https://www.chicagobusiness.com/residential-real-estate/chic...)