New York vs Chicago City compare? in 2020

New York vs Chicago compare? in 2020

I’ve briefly lived in Chicago and traveled to NYC extensively over the years, probably in excess of 50 times. Having a good understanding and appreciation for both, I would say for overall quality of life, Chicago hands down.

Now before a bunch of New Yorker’s take umbrage with me, I will point out the following:

NYC is an AMAZING place to live if you are filthy, stinking rich. It has everything, is a 24 hour city, and unarguably the center of the universe. I love the Upper West Side, SOHO, Greenwich Village, Central Park… but to live there and have a quality of life is prohibitively expensive, so most people end up living in tiny apartments that they pay way too much for and working incredibly hard to maintain a minimal lifestyle.

Meanwhile, a few miles to the west…

is a beautiful (but cold in the winter) city that offers a lot of what NYC has but on a more livable, affordable scale. Like a big city feel? Chicago has that in spades. Want over 20 miles of parks and beach along a beautiful lake that looks like an ocean… steps from the heart of downtown?

They have that, too. Want amazing food… at affordable prices? Chicago may be the best city in the country for that. Want to walk down a historic river with incredibly beautiful architecture and restaurants, pubs, galleries, etc? Chicago has you covered.

But what really separates Chicago from NYC is… you can afford to live there. Chicago will be roughly half the price for the same type of apartment/house.

The overall cost of living will not be terribly different from many other places in the country. Not having to pay $$$$$$$ to live is less stressful and allows for a fuller life outside of work, which as I get older, becomes more and more important to me.

Is it better to live in Texas or California?

New York vs Chicago compare
New York vs Chicago Food compare

So while I love them both, as far as living in one or the other, give me a condo with a lake or river view near some great restaurants in River North or the Loop—even the Gold Coast—and I’m home.

New York vs Chicago City compare? in 2020

I lived in Chicago for 4 years and currently live in NYC (been here since 97 w/the Chicago hiatus in the middle). I would obviously dismiss the opinions of anyone who actually hasn’t lived & worked in both cities.

To me, this is an absolute no-brainer: NYC. Though Chicago is pretty and has the outward trappings of a metropolis, at the end of the day, it’s overwhelmingly provincial (you’ll note that everyone who protests this is from Chicago or other place in the midwest), segregated (literally demarcated by “Northside” and “Southside”) and blatantly racist.

It is the “Mecca” of the midwest and all the folks from the flat states migrate to Chicago believing they’ve made it to the “big city” not realizing it’s just a lot of ignorant, narrow-minded people like themselves who think Chicago is the cat’s pajamas.

Don’t get me wrong, I’m not trying to be overly harsh and there are great, open-minded people around, but the proportions are all wrong and without typical social, peer feedback that racism is wrong (or at least should be muted), it thrives there, right out in the open.

NYC is the “Mecca” of the world; it’s the center of culture, fashion, media, and finance and there is no place remotely like it. Sure, Chicago has a nightlife and a dating scene (what decent-sized city doesn’t?), but it utterly pales in comparison to NYC.

New York vs Chicago City compare in 2020

You’ll meet people from all over the world and from all walks of life here, not a single or small handful of archetypes. The NYC public transit system knocks the pants off Chicago’s, by the way. No comparison at all.

Regarding the startup scene, there are really only 2 places in the US that matter as tech hubs—Silicon Valley and NYC. The tech scene in NYC is booming, being home to Google’s 2nd largest office outside of Mountain View, and a huge swath of startups and more mature tech companies.

Sure, NYC can be a harsh mistress and weak people will get eaten alive (or claim they like their own city better when they end up leaving), but there is always palpable energy and allure to NYC that cannot be denied.

Obviously, NYC will be far more expensive (think $1500 for a 1bd in Chicago vs $3500 in NYC), but if you can find a decent job and manage your finances, you shouldn’t even think twice about moving to NYC.

London vs NYC

This a no-brainer. Chicago.

  1. It has a growing tech-scene so I guess it would apply to you.
  2. It is very clean. You would find all other big cities in the dirtiest cities in the US except Chicago.
  3. It is pretty. It gives you the best of NY (architecture) without trash and shabbiness. Visit Times Square during the day and know.
  4. If you like to live in a developing world like atmosphere, you can stay in NY. I am originally from Calcutta, India. And I find the crowded, sweaty and smelly subway trains, open trash and the not well-ventilated subway system in NY which I wanted to escape.
  5. It is at least twice as cheap. My labmate who is graduating is going to stay in a 19 by 12 feet studio for 2700 dollars. I.e. is 30 % more than my grad student salary.
  6. People are friendly and nice. This is in bold as for me this is most important. In NY, its a city where you struggle and sweat. In Chicago, you share and care.


I don’t know who you are and what kind of personality you have, but I can tell you the risks / benefits you get from both cities.

Professional Connection:

If you’re a social butterfly and can get into any social group you want, I would go with New York. I say this because people in NY won’t have the time to / won’t make the effort to get to know you unless they don’t have friends. So, you have to have the skills to make them like you.

There are a lot more connections you can make in New York that can relate to what you do, and then from there on maybe, you can find fun. There are a lot of people in both cities, and it would be impossible to meet them all, but I think there’s a higher chance of you meeting more people in tech in NY than in Chicago.

Social Life:

If you’re not a social butterfly and used to have a good group of friends in your home town, you might feel lonely in NY (Current experience). Chicagoans are more down to earth and they are easier to talk to.

The chance of you making a close friend in Chicago might be higher than in NY. Nightlife I like it in both cities, however, there are more bars in NY than in Chicago.


Chicago has waaaaay better food for the price. New York just has more options and has more expensive food. So far, there hasn’t been a restaurant in NY (<$100 per person) that blew me away yet.


My friend in Murray Hill has a killer view of the Empire State Building, but his rent is like $1800 and he has to share a room with another guy 1/3 of the year.

You do t really get to see the skyline of Manhattan unless a) you can afford high rent, b) you’re across from Manhattan, or c) at the right rooftop bar.

Skyline in Chicago is so much better, and you can just go to the lakefront or Millenium Park and turn towards the city.


There are so many girls in NY. It’s insane. Walking down the street where all the restaurants are on a weekend, all you see is just girls getting brunch. They are everywhere. Although they might have very high standards on the guys they date – there was this one time,

I walked past these two girls in their 20s. They were talking about the dates they went all, and all they talked about was how lame their dates were. I think Chicago girls wouldn’t judge you like that, but of course, there are nice, smart girls in NY.

I always think that if I was single in NY, I would never get a boyfriend because there are so many good looking and competent women in the city.

Rent: Needless to say, Chicago is cheaper.

Would you rather live in Florida or California and why?

New York vs Chicago compare
New York vs Chicago compare

Both (New York vs Chicago) are fantastic cities…

If you want diversity….NYC wins hands down

If you want affordable rents…..Chicago wins hands down. Your money will go a lot further and you won’t have to get roomates

If you a single man….Slightly in favor of NYC. Chicago has tons of women as well. Can’t go wrong with either.

If you are a single woman….Chicago wins hands down.

If you want to escape for a cool day trip to a new city…NYC hands down. Within 4 hour bus ride of other great cities like Boston, D.C. and Philadelphia.

If you like nature…NYC wins. NYC is an hour from Hudson Valley which has all the outdoor activities you could ever want. Skiing, hiking, wineries, etc.

If you went to school in the Midwest…..Chicago wins hands down. The city is full of Michigan, Northwestern, Nebraska, Minnesota, Iowa graduates. Networks are strong if you went to these schools.sea

If you want 24 hour access to food and entertainment….NYC wins. Places like this can be found in Chicago, but not on the level of NYC.

If you are looking to buy a home…Chicago wins hands down. Although the taxes are sky high, they still pale in comparison to the suburbs of NYC. NYC is surrounded by 3 of the top 10 most expensive counties in the United States. Rockland, Westchester, Bergen. Unless your loaded with money you won’t be able to afford to buy anywhere near NYC.

Overall, the two cities are my favorite. If I had family in NYC I probably would have settled down, found a nice partner, and made it work.

Hope this helps! Whatever decision you make, I am sure it’ll be a good decision.

New York vs Chicago compare? in 2020

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