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setting -- nyc (I'm partial to the ocean over the lake)
food - nyc (although we are not to be trifled with, given the reviews of chicago restaurants I keep reading in the nytimes)
architecture - chicago
skyline -- toss-up (don't care to debate)
affordability - chicago
vibrancy - nyc
use of waterfront - chicago by a landslide
music/theater/cultural events - nyc by a landslide (although chicago has an excellent fringe/storefront theater scene)
.... I've never been able to quite answer this question myself. I like both, have only lived in one, but have visited the other many times. There are certain things that can only be found in nyc, and for that alone they probably eek out a bit more of my favor, but I'm not packing my bags to move there, I'm content to visit. That being said, nyc is three times the size of chicago, so I've never really understood how this is even a fair question, to be honest, I find them rather hard to compare, I think they are pretty different cities with a different orientation to the US and a different culture (I've got family from nyc, and so i've heard their impressions of chicago, which obviously wasn't too poor of an impression, as they choose to move here).
Setting - New York (Close to major other major cities, ocean moderates temperature significantly (not nearly as cold as Chicago).
Food - New York (Though Chicago has its own style of excellent Pizza, New York cannot be messed with when it comes to diversity of cuisine).
Architecture - New York (Perfect mix of old and new skyscrapers, diversified mix of housing (detatched houses in Queens and Staten Island, brownstones in Harlem and Brooklyn, sleek apartment buildings in Manhattan).
Skyline - New York. Breathtaking view of skyline no matter which angle the city is approached. More skyscrapers, outstrected skyline.
Affordability - New York. If you cannot afford Manhattan you live in one of the outer-boroughs. Where do you live in the city of Chicago that is not dangerous?
Vibrancy - New York. I've never really thought of Chicago as being vibrant. Just the 3rd largest city in the United States.
Use of waterfront - New York. Hudson River Park, Battery Park City, South Street Seaport, Chelsea Piers, Coney Island. New York has too many waterfronts to even be messed with.
I'm a Chicagoan, so it's no surprise that I prefer Chicago (although I just got back from another New York visit and I must say that I love that place). I'll go through the factors:
(1) Setting: New York - Combination of history and cutting-edge residents in all facets of life.
(2) Food: Tie - New York gets the edge on the high-end (although Chicago has been extremely inventive, as well), while the everyday foods such as pizza and Italian beefs go to Chicago.
(3) Architecture: Chicago - Sleek skyscrapers, brownstones on the residential neighborhoods, the birthplace of Mies Van Der Rohe's modernism and Frank Lloyd Wright's Prairie style.
(4) Skyline: Tie - Both are stunning - I can't pick one over the other.
(5) Affordability: Chicago - Not even a contest. I'm not sure what miamiman was talking about wondering where you would live in the city of Chicago that's not dangerous - most of the city outside of the deep South and West Sides is gentrified. It's way nicer than the outer boroughs (NYC really needs to take some lessons from Mayor Daley about cleaning up graffiti and trash), closer to the lifestyle in Manhattan, while being about half the price.
(6) Vibrancy: New York - Chicago has a great nightlife scene, but NYC is a true 24-hour city.
(7) Use of Waterfront: Chicago - Almost all of Chicago's Lake Michigan shoreline consists of immaculately maintained parks and beaches along with draws such as Millennium Park, the Lincoln Park Zoo, and the Museum Campus. At the same time, the Chicago River has been the focus of increased development in the Loop. New York has a few great areas such as New York Harbor, but its use of its waterfront is more spotty.
Affordability - New York. If you cannot afford Manhattan you live in one of the outer-boroughs. Where do you live in the city of Chicago that is not dangerous?
Spoken by someone who has obviously never been to Chicago. You have got to be kidding me? I've lived in MANY parts of Chicago for over a decade that were not dangerous at all. I currently live in what is probably equivalent to Brooklyn's Williamsburg neighborhood in chicago, perfectly fine place, there there are a couple of purse snatchings here and there, but are you going to tell me that doesn't happen in new york? I think you might have watched too many movies bud.
Do not get me wrong, I myself prefer many aspects of new york over chicago in many areas (not all though), this is not blind boosterism, but to say that there is no part of the city of chicago that one can live in that isn't dangerous is quite frankly absurd (I am living proof of this), and entirely as untrue as believing that all of new york consists of Manhattan penthouses (as my Grandfather from the Bronx would certainly be happy to inform you about).
Setting: NYC for the simple reason that a short drive will get you into the mountains (not hills like IL has).
Food: Tie. NYC and Chicago both have inventive foods from every nationality you can think of, and in abundance too. I cant remember the magazine, but some mag voted Chicago as having the best chefs in the nation, but then again NYC has also claimed that for many years. As for everyday foods, Id have to give Chicago the nod. Deep dish or NYC-style pizza? I like em both. Were the only 2 cities in the nation that can do a mean pizza. LOL Overall food? Just too hard to tell, hence the tie in my books.
Architecture? Chicago. Father of the skyscraper, home to the tallest buildings, immaculately maintained historical buildings, wonderfully diverse architecture on every street. Most architectural gurus will rank Chicago over NYC, Id have to agree with them.
Skyline? Another tie. NYC has a HUGE skyline, but parts of it are quite boring. If youre going for overall size, NYC definitely wins. If youre going for diversity and beauty, Chicago. Its just perfectly laid out. Plus the lakefront opens up the whole east side of downtown, so it feels so much more "open".
Affordability? Chicago, hands down. Miamiman must not pay attention to housing costs in both cities. Sure Chicago is massively overpriced, but is cheap compared to NYC.
Vibrancy? NYC, just because its 3 Xs larger than Chicago. Chicago is a 24 hour city, but not quite as much as NYC. Theres no shortage of vibrancy in Chicago, obviously. Its just not on the massive scale of NYC. I also have to question Miamiman's logic regarding "vibrancy". Clearly hes never been to Chicago. LOL
Use of waterfront? Chicago, by far. From downtown up to WI, almost every inch of the beach is utilized in one way or another.
This is a neat poll. However, comparing Chicago to NYC is kinda strange, based on size differences. With that being said, Id give the trophy to Chicago, not just because I live nearby, but because it offers everything NYC does, for cheaper. And since its only about 1/3 NYCs size, I think thats amazing! Chicago is and always will be my fave city in the nation... its just so... American. Its beautiful, diverse, cheaper than the coasts, offers distinct 4 season weather, beautiful lakefront, arts, sciences, abundant jobs (good paying too!), excellent cuisine, etc, etc, etc, etc. Frank Sinatra didnt write a song about Chicago for nothing. LOL And that was back in the day! If he could only see it now....
As someone who has lived in and around NY and visited Chicago plenty when I lived in the midwest, Chicago just is way more appeasing to me. I would never consider living in NY again. It was a choice made my father years ago that I had no control over then and I just never to this day understood some of the appeal of NY outside of Manhattan. I would give the nod to NY for overall food even despite the fact that I hate NY style pizza in most instances. Regionally speaking I'd prefer to be in the vicinity of what is offered outside NY rather than Chicago and weather is slightly more tolerable in NY. But for the outdoors, aesthetics, bar scene, cost, people...Chicago easily outdoes NY in my book.
Setting - New York (Central Park, the vintage brownstone buildings, Fifth Avenue, bustling Times Square, Wall Street and the classic Financial District, the Statue of Liberty, skyscrapers, trendy different districts, nicer weather than Chicago not as bitter, Tavern on the Green, the George Washington Bridge, the Staten Island ferry, the Palisades, Long Island, Tappan Zee Bridge, leafy Connecticut suburbs, the bridges and tunnels.)
Food - New York (Many more restaurants, best Italian food (only good New York style Italian I've found in Chicago is Volare's on grand avenue)
Architecture - New York (beautiful old historic doorman buildings, vintage brownstones, trendy loft spaces in the Village and Chelsea), modern apartments and skyscrapers, classic lush hotels like the Waldorf-Astoria and the Pierre, the fabled "pre-war six", the apartment from Breakfast at Tiffanys
Skyline - New York - water on different sides, the riverside drives, Central Park + views, skyline can be seen for many many miles in each direction
Affordability - Chicago. Overall, a much better deal. However, you have access to jobs in New York that can pay even more than in Chicago and more career potential. Chicago burbs not a whole hell of a lot cheaper than New York and the New York burbs have more soul to them and nicer looking houses/landscapes.
Vibrancy - New York.
Use of waterfront - New York. You got the ferries, the riverside drives, tunnels bridges, the Central Park ponds and sailboat race, the Hudson River and the Palisades drive, Long Island beaches, parks and boats in the city itself. Chicago has got the lakefront and you can use it more than you can in New York and bike along the lakefront but the New York area has a better use of waterfront over all and the lakefront itself.
My favorite area of Chicago is the Gold Coast - Delaware Place, East Lake Shore Drive and some of the Vintage Buildings. The Drake Hotel and the North Michigan area remind me of new york city particularly in the fall.
For the most part though I feel that Chicago lacks the romantic feel of place that you can find in New York. The ultimate in city living is a vintage brownstone on Central Park West with a doorman a couple thousand square feet, park views, and a cast iron clawfoot tub. Think Panic Room with Jodie Foster. People tell you about the Upper East Side but I like the Upper West Side cuz its just as pretty if not prettier, cheaper, and more low key.
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