Raising a family in Chicago. We like it. Had a bike stolen. Not sure how best to help the poorer areas of the city. Me moving out of state won’t help them, I don’t believe.
Raised in Florida, live in Chicago (old town) with kids. Walk to work (and drop off kids at school); 1.75 mile walk. Walk all year. Weather is fine above -15, which it only hits a couple times every couple of year. No special breathing required, though you need to bundle up. Rain is the worst to walk in. We have a car, but used mostly for golf.
I think with restaurants, art scene, theater, and parks, it beats other affordable cities (not sf, nyc) in my mind. But it doesn’t have the outdoors fun of the West. If we leave, we may go very rural. Taxes and financial trouble do make me a little nervous, as a property owner.