If it took the fall of the World Trade Center for the world to see that New York City has a heart, then Chicago only needs a hangnail.
To a person, including the street guy who wanted me to give him 10 bucks for a room for the night, Chicagoans are universally nice people. Doormen, servers, street sweepers, counter people, doesn’t matter. They’re just nice folks. They don’t mind giving you directions, or sending you on the right path. They don’t seem to mind idle chitchat to pass the time. They also don’t seem to take themselves that seriously. Baseball, Football and Basketball are Serious. But the rest of life is more relaxed.
New York City, in my pre-9-11 experience, was an essentially grumpy place. There was a move afoot to change the state motto on the license plates from “Empire State” to “You’ve see it, now Fuck Off” NYC also had too many people per square foot for my liking. Chicago is just as population dense, but it doesn’t seem as oppressed by it.
Downtown is a skyscraper canyon like NYC. A few zillion folks commute in every morning and zoom out every night, but the attitude is more of we want to work here, not we MUST work here.
RoadDave 
For years, my dad told a story of being approached by an older lady, asking for “car fare to Glenview” (one of the suburbs) as he left Union Station, one of the big commuter railroad stations. For over ten years I heard, about once a month or so, of “car fare to Glenview”. Time passed, and I scored a job working in downtown riding the Milwaukee Road into Union Station. One glorious morning, I decided to take a slightly longer way to work. A block from the station, this nicely dressed prototypical “little old lady” walks up to me and asks if I can help her. After I said yes, she launched into a story of how she had come into town for some reason to help her son, something happened (I don’t remember what), and she wound it up with a request – you guessed it! – for “care fare to Glenview”! The same lady who had hit my father up countless times! I don’t think she understood why I mumbled something incoherent to her and walked away, laughing my HEAD off! I did manage not to laugh in her face, but only by literally chewing my cheek until I bled (hence the incoherent response to her). I laughed for the rest of the day – solidifying my reputation at work as “that strange guy with all the Star Trek autographs”.
God I miss Chicago!