At your own risk
Lived here for five years, right downtown for three, and two at the end of the Brown train line, a close suburb known as Ravenswood, commuting in to the city for work. Like they say, Chicago is a quilt of neighborhoods, and outside of the Loop (downtown), few buildings are above 3 stories. So there are many Chicagos, but the differences have blended. Basically, you have the north (white, hispanic, Asian) and the South (a black war zone, with a few heavily guarded enclaves like U of Chicago and some older white blue collar neighborhoods full of cops.)
There is undeniably a lot of good in Chicago, if you can afford to enjoy it. But the place grinds you down; the pace, the costs, the crime, the corruption, the intensity, the grunge, and THE WEATHER. I was a professor at a very famous museum and art school downtown, and my time in Chicago was spent very much in the thick of things. Moving there I sensed that I had about five years tolerance to it all, so made the most out of it, and sure enough, moved away almost 5 years to the day, exhausted and pretty fed up with the place.
The reputation for corruption there is NO JOKE. This has effects in every aspect of life. The fact that half the city is a war zone more dangerous than Baghdad or Mogadishu, even if you never experience it first hand, has effects. And you can live in the north parts of the city and never hear a gunshot, never get mugged, or worse. It can seem pleasant and peaceful. But the place is still run by crooks, is inconceivably violent, and is still a disaster. The latest mayor is the worst yet, but those that proceeded her were hardly much better. The schools? The teacher's union? Unbelievable.
So of course the food is fantastic, the cultural institutions are second only to NYC and superior in some cases, the lake is nice, the 8 weeks of summer pleasant. I like cold and snow, so the winters didn't do me in like I watched them do to most others, but still, by April you are worn out. I've only watched all the BLM Antifa stupidity there this last year on TV, and its hardly isolated or even worst in Chicago, but there are a lot of people ginning up a race war, and the situation in Chicago is a powder keg. So-called "white" folk are getting assaulted every day just for their presumed skin color; I was more than once stalked and nearly mugged, but for my awareness and taking steps (ducking into stores, jumping off trains last second and sprinting out of stations, etc.) Woke-tardation and Trump Derangement ARE the politics there; communists, blue-haired tattooed feminists, and pride-full gays run every cultural institution, and angry black women and lesbians the politics, so expect to just live among people who are completely out of touch with reality and basic sanity.
Chicago is Chicago. It sprawls forever on a neverending pancake plain, so don't expect to hike or anything. The city is resented by everyone else in the state. Still in my top three cities to visit, to visit the museums, see a show, eat great food, drink in dive bars. I'd warn anyone to never live there.
Matt | Denver, CO