Former Chicagoan here. Grew up in Evanston and lived in Lakeview area for almost 20 years. We moved to a small town in Colorado a few years ago. Chicago is just constantly running against the wind. Violent crime is a game-changer (property crime is one thing, violent crime another), public schools are dysfunctional, taxes are bad and only getting worse, weather is terrible the majority of the year, and there's nothing particularly interesting to visit within a few hundred miles (though I've always loved western Michigan). Chicago has a culture that's gotten progressively uglier and makes a lot of people generally not want to live there. I could go on, and I'm not saying anything unique. It's just running against the wind and prevents Chicago from ever really taking off and reaching escape velocity. It would take a real unicorn to jumpstart things more.
Btw you ask any former Chicagoan and they'll say the same thing: their only regret was not moving sooner.
Btw you ask any former Chicagoan and they'll say the same thing: their only regret was not moving sooner.