Chicago v.s. New York

I recently visited New York a couple weeks ago and couldn’t help but compare the most populated American city to our fine city (third most populated in the U.S.). I performed no research and am expressing my clear perspective & opinions on some contrasts that most always wonder…”how does Chicago measure up to NYC?”

NY – It’s true. Everyone is in a hurry. There is little to no patience amongst the NYC—where motorists frequently use their horn to let you know how little they will put up with you terrible, overly-cautious, or slow driving. There are lots of cars, lots of people, little space, a bunch of ‘one-way’ roads, and sparse parking.


CHI – Our city is like any other big city. Always a lot of people, lots of traffic. I’d say are traffic is on par with most cities in the U.S. top ten cities for population. Although it’s not as bad as L.A. or New York.
NY – Kind of complicated! Most people use the subway system, which is bigger and a tad, only a tad, quicker than the CTA. The MTA, as they call it, is usually congested with few empty seats between people seated. Like in Chicago, when lines or stations are closed for repair/construction it is an absolute bitch to get around via the subway. Buses not as updated as the CTA’s. Taxis are in abundance yet hard for minorities to hail. Airports are tighter about security (for obvious reasons).


CHI – The CTA is slow. Taxi service not bad but getting pricier. Both airports have their drawbacks and there are fewer buses with longer wait times now than there was a few years ago.
NY – First time I have been to a major American city where trash is wrapped and thrown on the sidewalks for garbage men to pick up. There are little to no alleys in NYC. Pollution varies from neighborhood to income level of residents… same as ay big city.


CHI – Definitely cleaner than New York overall. We do have alleys for the placement of trash and our buildings our reminiscent of New York’s but less aged.
NY – It’s statistically bigger than Chicago and felt huge. More over because I navigated throughout Manhattan and most of Brooklyn and still had 3 more boroughs (Bronx, Queens, & Staten Island) left to explore.


CHI – Our city is huge! But not enough to beat New York. We have the beautiful Northside, gritty Southside, the lovely lakeshore, downtown area, and the wild wild Westside.
NY – Not as rude as most people believe. Whenever I needed some assistance, all I had to do is ask and someone would try to help me. They for sure are less patient with workers in the service industry, I felt, have a short fuse when dealing with stupid questions and annoying people.


CHI – Always very courteous, helpful, and kind. There will always be douchebags in the mix but I feel we don’t have any above normal levels of pricks in our fair city.
NY – The women were more diverse—meaning something for everyone. They are more superficial than Chicago girls but less were childish. They’re dressed in the latest fashions and pretty independent. I don’t know if it was just because I was out of town but I was impressed by the differences that I still have trouble describing without putting our city’s women down.


CHI – Sorry but for the most part women in Chicago are just as beautiful as NYC women but the ratio of hot women to average chicks is lower here than in New York. Not just that but New York women standout more and are more fashionable. One thing that our women have though are those midwestern values.
NY – Empire State Building. Statue of Liberty. Brooklyn Bridge. Central Park. Yankee Stadium. Madison Ave. Fifth Ave. Coney Island. ICONIC ATTRACTIONS
CHI – The Sears Tower (Willis Tower I should say). Wrigley Field. Navy Pier. Millennium Park. Hancock Building. Michigan Ave. Lakeshore Drive.
NY – New York Yankees


CHI – Chicago Blackhawks

Hard to compete against Gotham city but I feel Chicago holds its own. I’m pretty sure a New Yorker living in Chicago would marvel at how the pace is nearly the same yet we’re more chill, just as polite, cleaner, cheaper (well… depends), and probably a better place to live.

Comment on who you, objectively, think is the winner of this ‘head-to-head’ battle and why. If you have a category, that I should add and compare the cities on, feel free to comment—and I will update the article.


  1. Kathy says:

    Look, don’t rate woman like they’re something that you can just flirt with. We all have feelings, and woman who read this are going to feel bad about themselves because, they don’t feel like they are good enough. Just because you are born some place does not make you look any different from people in other places. If your going to do that, atleast do men as well so people won’t get as bad as an idea of it.

  2. some dude says:

    why do people always have to get online and cry about their feelings. kathy, ur probably just made because men never notice you, so dont get mad when everyone else gets rated and u dont get a second look.

  3. Oleg says:

    I lived in NYC for two years and visited Chicago few times, was planning on moving there.
    Chicago is a little ”less” : Less expensive, less crowded, not as dirty, etc.
    Overall I’d say Chicago is better, but it’s different for everybody =)

  4. Suprised says:

    Alright, I know you probably didn’t mean anything bad by it, but I am a 25 year old white male from the chicago suburbs, I know your a Haitan-American, but just a heads up. If your trying to sound professional, you cant use ‘Women’ as a category of attributes the way you did my friend. It comes off as sounding like women are just another part of the scenery without comparing men as well. Most educated Americans will find the way you have worded that part of your comparison to be somewhat offensive.

  5. Tom says:

    Nothing wrong with rating women. They want to be objectified. Except Kathy, because she’s fat.

  6. Amanda says:

    I’ve visited NYC and Chicago in passing and spent 1 day in both cities. I was drawn more to Chicago. My comparisons of the cities: Chicago has an old feel to it, historical. I walked the streets and a sax player was playing and it echoed off the buildings. That was very cool. The Hard Rock Cafe and Sky Deck is AMAZING. Traffic wasn’t too bad. People were nice. It’s clean and beautiful. NYC is amazing as well. However, traffic is a nightmare and you have to pay to do anything-tunnels, bridges, parking garages because you can forget finding a parking spot. The people are either nice or rude. Both cities are beautiful and iconic. As far as the “Women” comment goes, I’m a 27 yr old woman. I was not at all offended by the comments. I think that men would want to know about women in the obvious ways but women probably because of the fashion. The don’t want to go to one of the most popular cities for fashion feeling or looking out of place. Chicago is still full of fashion forward residents as well but NYC is expected to be that way. Men aren’t as fashion forward as women. There’s plenty to see in both cities and I plan on making my husband take me to both cities again and stay for about a week in each one.


    why do people always have to get online and cry about their feelings. kathy, ur probably just made because men never notice you, so dont get mad when everyone else gets rated and u dont get a second look.

    why do some dudes have to get online and trash other people for having feelings. some dude, ur probably just feeling GUILTY because you know you have no respect for women and one day you are going to need a woman to help you out of your bed in your old age and there won’t be one to help because you trashed all women!

  8. thebombshell says:

    well i like bth but team la

  9. faily man says:

    i like both their cool but i rather like paris

  10. jordan says:

    Nyc hands down. I’m from the brox and have family in chicago, so i always go and visit. Chicago ppl arr very lat with fashion. Sorry to say

  11. Andrew says:

    I have lived in both, its pretty much the same. If your standing between 2 tall buildings the sun dont shine no matter where your at. NY is a little more polluted. I am used to it though i’m a city boy, grew up in the city (not the burbs) As far as the women, i never noticed any difference, But i only dated gorgeous women so i pretty much dont notice average or fugly women. And hey, if she could carry on a conversation that’s a PLUS- but not a requirement. If you think Chicago or New york suck- Go spend a month in Boston and you will be glad to get back to either. And both citys have good food

  12. Anonymous says:

    Here’s the thing you need to know. People in Chicago think about New York, but not the other way around.

  13. Nicole says:

    I beg to differ! As a Chicagoan turned New Yorker, then reformed… I say New York beats Chicago hands down for everything you listed. I hate Chicago.

  14. OGreen says:

    Here’s the thing you need to know, I never knew a Chicagoan to say anything about NYC unless I asked them, so I must disagree with “anonymous,” the mind reader. People in Chicago are not thinking about New York. Why would they? Chicago has everthing, including a stunning downtown lakeshore, replete with downtown beaches.

  15. Anonymous says:

    NY sucks Chi Town will kick your ass

  16. Swervee says:

    Chicago is “okay” for a city. I mean you guys have Kanye and the sears tower but for crying out loud NYC is better. We got the upcoming freedom tower which will be the tallest building in America. And the second tallest in the world. And we are where hip-hop/rap started. We also have the best McDonalds which has 5 tiers and we have the best football team who has won 4 consecutive Super Bowls with 1 coach. So this is why Chicago is “okay” for a city.

  17. Anonymous says:

    You forgot to mention the skylines. I have been to both cities and believe that Chicago skyline is hands down better.

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  19. Anonymous says:

    America has only 4 well desirable cities for educated and professional urbanites which becomes a topic of comparison and rivalry.

    1) New York – the World’s Greatest City

    2) Chicago – America’s Quintessential City

    3) San Francisco – America’s Most Innovative City

    4) San Diego – America’s Finest City

    Each to his/her own when it comes to squaring off which city is better, especially with NYC.

    Chicago is indeed a great and nice city. But because it’s in flyover territory, it takes a backdrop because the Northeast and California seems more important.

    San Diego isn’t a hustle and bustle town like the others, but’s with its resort beaches and overall beauty, it captivates those from the other cities. Think of it as a cool hangout akin to a top notch bar or restaurant where one takes a break.

  20. Chitowngirlable says:

    I live in Chicago and have visited NY for a whole 2 weeks. The states are so similar yet so different. Chicago has selected rush hours times and NY seems to have rush hour 24/7. I visited NY right after 9/11 and the people there were very friendly and I absolutely love their accent. As far as cost of living, I think NY is a lil pricier but certain areas in Chicago (Northside) can be ridiculously high too. Of course NY is dirtier because we have alleys. There is more history in NY, especially in Harlem! I covered every burrough, project, park etc. and overall I can say, I would be able to survive in either state but my preference is Chicago…

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  32. Max says:

    “Chicago is “okay” for a city. I mean you guys have Kanye and the sears tower but for crying out loud NYC is better. We got the upcoming freedom tower which will be the tallest building in America. And the second tallest in the world. And we are where hip-hop/rap started. We also have the best McDonalds which has 5 tiers and we have the best football team who has won 4 consecutive Super Bowls with 1 coach. So this is why Chicago is “okay” for a city.”

    Really? you can say New York is better than Chicago, I’m fine with that. but calling Chicago an “okay” city is ridiculous. since Chicago is the second city, your calling New York great, but all other American cities “okay-less than okay”? Plus the Sears/Willis tower is taller by actual building. you guys just plopped a huge stick there and called it a spire. also i don’t know how its good to have the “best” McDonald’s. the food is still crap! but if you think McDonald’s makes or breaks a city, then keep in mind that the first McDonald’s was in Chicagoland. not to mention that Chicago has two baseball teams one with the craziest fun fans but the suckiest team the cubs. we also have hockey, soccer, and basketball teams just like you. not to mention that Chicago was rated #1 for professional sports and sports bars in the nation according to the travel and leisure website and also beat you in pizza and architecture and cool buildings. this is a poll from visitors too, not residents. also we were #2 for luxury stores after New York which scored 4.80 points, while Chicago trailed close behind with a 4.71. Seeing from the facts Chicago is no “okay” city. The only thing New York has on Chicago is more people, more dirt, more costs, and more buildings (but not better buildings

  33. Max says:

    i forgot to mention the 2000 foot monster gathering finances in Chicago, the Chicago spire

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