I agree about "*** the Bears," but I disagree about Chicago. The four years I spent in Hyde Park were really great.
I lived on 57th close to Washington Park, then on Greenwood just south of 51st. I used to go out frequently after midnight on foot to get Harold's chicken, I shopped at the Jewel just south of 75th on Stony Island, across Stony Island and a couple of blocks south of the Nation of Islam's big mosque. I never had any problems at all. And since I left, that whole area has been heavily gentrified. For example, the regular-people grocery store at 51st and Lake Park where I used to buy IBC root beer is gone and has been replaced by a

Whole Foods

.
And culturally, those four years were amazing. I used to catch blues shows at places like the Checkerboard, Buddy Guy's Legends, B.L.U.E.S. (and I think a second location called something like "B.L.U.E.S. etc."), and the Kingston Mines. There was an awesome jazz show every week at the Blackstone Hotel. The Blues Festival in June, the Taste of Chicago in early July, and the Jazz Festival in September were all very much worth attending. The Art Institute deserves its fame, and I enjoyed multiple expositions at the Smart Gallery. Plus a math-and-science nerd like me couldn't miss going to the Museum of Science and Industry (I used to refer to it as "µ Sci & I"). Some major musical artists (and some minor ones I liked) played shows at the U of C, and many others played shows in the region. I also saw multiple shows by the Second City (sketch-comedy farm system for
SNL) and attended several theater shows. Food-wise, it was great too. I already mentioned Harold's, which is simply spectacular. One summer, a buddy of mine gave himself the mission of finding and and eating from every Harold's location. I went to many with him. I also enjoyed the gigantic (eat-with-a-fork-and-knife) burritos another friend and I used to get in a Mexican neighborhood well to the west of Hyde Park. I went to some snooty-but-really-good steak houses and Italian restaurants. And I came to really like Chicago-style Pizza (John Stewart can kiss my ass). I went to some of the famous places, but I enjoyed a couple of less-well-known places right in Hyde Park (on 57th heading over toward Lake Park, I think) at least as much as I did the famous places. And the Taste of Chicago let me try something from each of a $#!+load of different restaurants around the city each summer.
If I had to, I'd live in Chicago again and be pretty happy about it, except for the damn cold. I lived for over 12 years in Maine (and for a few months, including a winter, on top of a mountain in Switzerland) and thought I knew what cold was until I moved to Chicago and learned that there were whole other levels of cold. In Chicago, I got about a week's worth (usually broken up into two or three short stretches) of days each winter that were at least as cold as the two worst days I can remember from Maine winters. And honestly, I don't think I'd want to spend another winter even in Maine. If I never have to step in slush again in my life, it will still be too soon.