Forgive me if I come across as a little defensive but I can't believe some of the Chicago "bashing" going on here. For the most part I think antirabbit's post is a great summer-upper with johnapril alluding to one of the main differences being that Chicago neighborhoods, in general, are "quiet" after about 6PM or so. It always seems like in NY that there is a persistent commotion and noise from cars, trucks, sirens, etc. that would suck the soul out of me if I lived there. In most Chicago neighborhoods you can relax in relative peace once everyone is home from work. Don't get me wrong, I love NY and like the energy...but can't imagine confining myself indoors all of the time to get a little peace and quiet.
As far as Chicago doesn't have this or that...it's BS. I've lived here for 40+ years and
I haven't scratched the surface of what the city has to offer. If you haven't found food you're happy with then you haven't gone to enough places. Just like NY, people from every country in the world end up here and open restaurants. I'm sure it's the same in most big cities where there's a "Chinatown", "Greektown", "Little Italy", etc., etc...it's no different here. I'm not big on Chinese and haven't been to Chinatown in decades but you can always drive 10 minutes west to Oak Park and try Flat Top's. Someone mentioned fusion and there's a lot of that downtown...Roy's comes to mind. Don't get me going on pizza because that was a
whole other thread, but my point is that some of the greatest chefs, restaurants and food can be found in this city (even though Smith & Wols is still my favorite steakhouse).

And movie studios, hundreds of theaters, the Symphony Orchestra, the Lyric Opera House, the Joffrey Ballet, the Art Institute, the Field Museum, the Museum of Science and Industry, the Adler Planetarium, the Shedd Aquarium, the Lincoln Park Zoo, the Brookfield Zoo,
7300 acres of parks with 33 beaches, 9 lakefront harbors, etc., etc., etc. Not to mention a burgeoning fashion scene, just about every major designer being represented on the Mag Mile, HSF and Oxxford founded and based here and a renowned tailors like Chris Despos.
I could go on and on and on about all the things that make the city great (and even better than NYC in some ways) but the reality is Chicago doesn't have 20 million people. It doesn't feel the international influence NYC does. It is still a world-class city though (with a kind of small-town feel and sensibilities).
As far as livability, Chicago was built on a master plan that integrated commerce, transportation and recreation. The beauty of the city is that you don't need a car and can get just about anywhere on public transportation. Many people walk to work and from home can often walk to the grocery store, restaurant, coffee shop, bar, to do their shopping or, in many cases, the beach or park. It is my understanding that real estate is about half the price as NYC but it's all relative with the Gold Coast being as expensive as it gets anywhere in the U.S.
As far as safety and crime, Chicago is as safe/violent as any other big city. For the most part, I believe, violent crime is pretty much confined to smaller pockets of concentrated gang activity. Fringe places like Hyde Park (and Oak Park for that matter) will have the occasional random act but it is far and few between. Many areas are totally segregated racially or ethnically while other neighborhoods are melting pots. While there are distinct differences between the more refined North and the more "blue collar" South sides I think Chicagoans all get along pretty well. In general people are friendly and lack pretentiousness.