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Living in Chicago and having spent some time in NYC and its Borroughs, I can only give you my biased opinion.
NYC Pros: More career opportunities if you are in T.V., Stage or Film (with the exception of Hollywood). A little bit better weather. Lots of new exciting stores and food eateries that seem to take forever to make it to Chicago.
Chicago Pros: A Big City that looks clean, fun and welcoming. More affordable than most places in NYC comparably. Midwestern values that matter to a lot of people still exist in this big city.
Having lived in and around NY, but having spent plenty of time in Chicago working and having visited many friends I had there, I just will never understand the NY hype. Never again will I live in NY. Fine to visit Manhattan here and there but day-to-day life, forget about it. Different strokes for different folks and I understand certainly if you are that much into Broadway shows, that you would attend on a consistent basis.
I'm not saying most urban cities are the bastion of personal freedom and affordable living and nor is Chicago an exception, but the biggest oddity about New York and the surrounding burbs I find is how anyone can honestly love government trampling on people's freedoms, babysitting you to death, fining you for sitting on milk crates on a city sidewalk: yes I'm not making that up, couretsy of that fascist dictator Michael Bloomberg. If anyone doubts that the Republican Party is not party of Reagan principles any longer, the best example is to look at this guy's track record: as despicable of a politician as any. It trickles to the suburbs. I lived in pretentious Westchester County for a time as well and I really believe you have to be warped in the head to roll over and accept the ridiculous taxes, fines for parking the wrong direction on DEAD END NEIGHBORHOOD streets, restricting every shape or form of housing renovations on your own private property, "PUBLIC" park visiting restrictions: yeah, yeah I know hundreds of other such places exist today somehow. But not to this magnitude, except perhaps San Fransicko. People in this county even have been polled and FAVORED being taxed MORE!- all in favor of shoring up that public education system in most towns that is only on par with most private schools across the country.
Who can enjoy living in such a police state? Long Island, Rockland County much the same. But also Westchester Co. stands out from those burbs for possessing the largest contingent of people in the country where there is nothing to do after dark! Even by day, I swear there isn't anything but a diner, or very subpar deli or pizzeria on every street corner (YAWN). Except perhaps White Plains, I've seen more vibrancy in the boonies of Connecticut. So I'm not buying the whole "burbs" argument either. I've been in Chicago suburbs to the north & west far more sufficient if you don't have the time/energy to stroll into the city: better food, nightlife, and much easier to get to beyond rush hour than areas like Long Island.
As for nothing beyond downtown, I wouldn't consider downtown to be Wrigleyville or Blues Alley around Depaul just as examples. Plenty going on there.
Again, alot of drawbacks, some similar to NY, do exist in Chicago. But I would live there in a heartbeat with the right job. I find Grant Park way more scenic, cleaner, and relaxing than any park in NY City. The city as a whole is cleaner and less stressful, just as exciting once you get past the Broadway aspect. Manhattan is a wonderful place too and very active, but this might be a closer battle if we were just talking Manhattan. The other four boroughs? Goodness, the scenery is even better in Toledo without nearly some of the crowding and cost issues.
I guess one way Chicago could be better than New York is that it is much more centrally located like St. Louis. With Chicago using a car to travel to a very good portion of the lower 48 is not farfetched, compared to New York. Chicago makes a much more ideal location for a business than New York I would think just because of its location in proximity to many other cities of the U.S. They really have a lot in common though considering both are major Northern cities...New York certainly has better weather than Chicago in the winter. Not sure about crime though...Chicago like any Midwestern city (i.e. St. Louis, Detroit, Cleveland) has a decent amount of crime. New York there is certainly more to do than Chicago...it just dwarfs Chicago with its overall size, the whole metro area is just enormous...just covers an unbelievable amount of distance.
Chicago's skyline is much better because it sits on the shores of a very blue lake. Its skyscrapers have colors unlike New York's stone ones. Chicago is better planned because Lower Manhattan is not part of a grid system. New York's grid is an afterthought; it's too bad that Center City and Lower Manhattan couldn't trade street plans.
I have noticed recently that Chicago is becoming more popular and New York is becoming passé. I think this happened because Manhattan has been popular for many years and it was time to try something new. Plus Mayor Daley has been sprucing up Chicago--remember the "Green" roof over City Hall? Don't forget it is THE bright spot in the devastated Midwest!
One thing that New York and the other East Coast cities have over Chicago and the rest of the country is the history. The Revolutionary War was fought there and this is where the United States started. I really like the historic charm of the East Coast.
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Ha!
