Chicago has issues yes, but so do all the big cities. Just because it has winter isn't a good enough reason to paint the entire region as terrible. And please don't say "crime" and "guns" and whatever else - there are similar problems everywhere.
I'll be interested to see what the top destinations are in 2025.
I have a friend that retired in Chicago and loves it. He considers it as a place with similar amenities to New York or San Francisco, yet with significantly cheaper housing.
I briefly visited and enjoyed the city. I only know it as a tourist, but it's on my list of cities to consider moving to once the kids are out of the house.
I have heard the great lakes area called a "climate haven" compared with places like California or Florida, but I don't know whether that's based on anything more than the lack of hurricanes and fires.
Yes this and what everyone else said about how fantastic Chicago is. It is hands down on my top 3 best cities in the US. I've not lived there just visited, but I have a couple of friends who live there full time. I've visited the city a fair amount, restaurants, Wrigley Stadium, arts, culture, music, that cheese and caramel popcorn they do so good, people are nice, the city is set up in a logical fashion, lot's of interesting things going on, I thought the public transport was good etc.