I own investments in Chicago and they've performed well. The market is also hot for purchases as I've written more loans than I can count last year. Not only that, yet a lot of people are refinancing and staying in their homes.
I like Chicago and the area in general as the ups and downs aren't as high and low as the coasts. Practically every other major city is on the coast and you can read about the real estate in places like California (in general), New York, Florida, Boston, etc. Chicago remains relatively somewhat stable and yet the demand remains.
When you hear about the "population exodus", just remember that more people does not mean more money coming and going. You can have a family of 7 leave, who live off a father's blue collar paycheck of $45k, only to be replaced by two single software engineers making $150k+ each. You'll read headlines that are written to get clicks and instill fear yet do not paint a full picture of the reality. This previous paragraph may sound grim yet it is what it is.