I have never been to Chicago but my US based family and friends both rate it highly as a place to visit.
I live in a provincial city that can get a bad rap too - for being boring, without a beach, and having a foggy climate.
While in one way these things are true, in other ways they are so wrong and the people doing the critiquing are often so ignorant and narrow minded. I played a game on one of them once, by having a bet how long into our conversation he would bad-mouth our city, and then when he did, telling him I had won some money!!