New York vs. Chicago - Where Would You Rather Live?

I'd be curious to hear folks opinions about this. NYC sounds great but is it really sustainable over the long run? Are the extra opportunities / amenities / people worth it for the cost and inconvenience? 

Comments (62)

Feb 14, 2021 - 6:03pm


"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

  • Prospect in IB-M&A
Feb 14, 2021 - 6:15pm

As an nyc native, I might be biased, but there is no city with the opportunity and amenities at that level. But that's my opinion ig

  • Analyst 1 in AM - Equities
Feb 14, 2021 - 7:18pm

give my take on it. Grown up in NYC (Tribeca/West Village) as well as my parents (Sunnyside, Greenpoint). I think the single best thing my parents did for me and my siblings was to let us grow up in the city and not a suburb. Just such a great experience and it is what I want for my kids as well regardless of the cost/lack of space. Being able to experience childhood in NYC just hits different and living here now with my non NYC friends, I can confidently say coming here in your early 20s for your entry years simply does not provide you the same experience.  

As far as the experience itself, NYC is literally the most diverse city in the US and possibly the world. Queens has been known to be the most diverse county in the world for a while. You simply don't get this diversity anywhere else. I am a white male and had a culture shock going to college where the super majority of people were also white which was not similar to my younger schooling experience. Schoolwise, so many top private schools as well as arguably two of the three most well known public schools in the nation in Stuyvesant and Bronx Science. Me and my siblings went to a combination of the top privates plus those two and had varying experiences but all amazing. 

Costwise it is steep. My parents are fortunate to have purchased a large apartment in the WV/Tribeca area back in the late 80s early 90s before the neighborhood was gentrified to be what it is today, but all the same, they love every minute of living here as they grew up in NYC as well. The experience living and growing up here well exceeds the cost. 

Most Helpful
  • Associate 3 in PE - LBOs
Feb 14, 2021 - 9:28pm

No one in finance will live somewhere where they experience Chicago crime... the bad parts are bad, no question, but you can easily spend a lifetime in the city without ever going there. The North Side, the Loop, etc. are all very safe. This is like Boomers in Iowa who think NYC is all like Harlem in the 70s

Feb 14, 2021 - 9:33pm

Chicago is cleaner and better for family life, and it's easier to get around (though NY's trains are more comprehensive as long as you stay in Manhattan). NYC is more vibrant and bustling. NYC definitely wins on food and nightlife, but Chicago holds its ground against any other city in the country there... it's just that NYC stands alone among American cities. Both have fantastic cultural scenes, sports, museums, etc. 


Personally, I think NYC wins if you're under 35, but Chicago remains one of my favorite cities in the country and if you want to save a little more, it's the closest you'll find to NYC in the US at half the cost

Feb 14, 2021 - 11:53pm

I've spent decent chunks of professional time in both. For me personally, I prefer Chicago


I am in Chicago over NYC right now for three reasons: (1) The people are nicer, (2) COL is way lower, both in terms of rent and entertainment, and (3) It's not as overcrowded


There are a couple common arguments the other way that I didn't find as important to me:

(1) "Not as much food / night life" -- no there isn't as much, but there's still a ton

(2) Worse job market / fewer ops -- depending on what you're interested in this can be an issue, but it also might not be. In these discussions some people always seem to think any job market that isn't SF or NYC is as bad as like Tulsa Oklahoma

Feb 15, 2021 - 12:59am

Chicago as of right now. I can get a luxury 1 bedroom for 1500 with state of the art appliances. For me, what matters is the day to day stuff. That means being able to live in a decent apartment in a safe area, good restaurants, and good public transportation. Living in Chicago straight out of UG I can afford a nice place, eat out weekly, and save a good amount of money. As someone who loves to cook, I have a 5 burner range and a new oven with plenty of counter space (and granite countertops). Sure, NYC has more to offer, but for the price? I do not think it is worth it. NYC has a good food scene, but Chicago's is probably 2/3. I just can't justify working so hard only to have multiple roommates in a shitty apartment. If I was making over 250k, then I would go to NYC.

Feb 15, 2021 - 11:39am

I'm not a big NYC guy, but the answer here is NYC without question, no? 

Commercial Real Estate Developer

  • 5
  • Analyst 1 in S&T - Equities
Feb 15, 2021 - 1:29pm

People are about to freak out on you lol. Somehow CHI is considered to be parallel if not better than NYC in every regard.

Feb 15, 2021 - 2:16pm


People are about to freak out on you lol. Somehow CHI is considered to be parallel if not better than NYC in every regard.

Didn't you recently leave NYC?

Feb 16, 2021 - 1:21pm


People are about to freak out on you lol. Somehow CHI is considered to be parallel if not better than NYC in every regard.

That's kind of weird to me, but I respect people liking Chicago. I didn't meant to trash it or anything - it's just NYC is NYC

Commercial Real Estate Developer

Feb 15, 2021 - 2:15pm


I'm not a big NYC guy, but the answer here is NYC without question, no? 

Is it so easy when it's NYC vs.  Atlanta? :)

  • Analyst 1 in S&T - Equities
Feb 16, 2021 - 3:06pm

They roll super deep here haha..I'm gonna just put up the white flag and say CHI is the best city in the country given the weather, lack of crime, quality of life, etc

  • Associate 1 in RE - Comm
Feb 15, 2021 - 12:46pm

Someone who is a 100% transplant to both areas (didn't go to school or grow up in the surrounding areas of NYC or Chicago) would enjoy NYC more.


Chicago is a great city, but NYC is just another level. Also, so many young, adventurous, ambitious people move to NYC every year so you won't be alone as a transplant. 

  • Prospect in IB-M&A
Feb 16, 2021 - 2:02pm

I can't speak for NYC; however, I grew up (and still am growing up sinceI'm only 19) in the North Shore suburbs of Chicago, so this may be slightly biased. That said, I feel like I am extremely lucky to have grown up in the North Shore. There is a stretch of VERY nice towns where I grew up that spans from Lake Forest/Libertyville (45 mins from Chicago) all the way to Evanston, where Northwestern University is. This is where a majority of successful families settle in Illinois. Speaking from experience, I will tell you that all of these towns are fantastic places to raise a family/grow up for several reasons: one, the high schools in this area consistently rank in the top 10 for Illinois and always produce loads of Northwestern/UChicago students, and two, if your children are into sports, this will be the best competition they will get in the whole state for any sport. No question. Anyways, I can't speak for what an everyday commute/traffic is like because I've never had to do that. All in all, I love where I'm from and if you lived here, I'm sure you would too!

  • Analyst 1 in IB - Ind
Feb 16, 2021 - 1:24am

1st generation Polish American that was born and raised in Queens,NY. I can't answer the question about Chicago because I've never been, but I have been back and forth between US and Poland. Growing up in Queens was amazing. I would say most of Queens is extraordinary for raising kids. Your classes are diverse. My elementary, junior high school, and high school classes exposed me to so many cultures, that I have never experienced "culture shock".

NYC has something for everyone, however, it has definitely gotten more expensive and continues to do so. Greenpoint is usually the first stop Polish immigrants would flock to when arriving in NYC, and it used to be a very sketchy area. Staying on the streets past 7pm was asking for trouble, and people would make fun of you for buying property in that area. Those same people are probably crying in their sleep after seeing how much change the area has gone through, and how dramatically property values have increased in Greenpoint.

If you're looking to for a break from the city, want to have a car to drive around with family and have a decent yard, there are many places in NYC where you can find that (Queens, deep Brooklyn, Long Island, Staten Island [although this is not a popular destination].In my part of Queens, it was so easy to find parking. The caveat of this was my work commute, which absolutely blowed. 

If you want to be closer to the city at the expense of having easily available parking, think Greenpoint and many other areas. There is something for everyone in NYC

I became a well-rounded person thanks to living in NYC, and indirectly learned to be street smart and out-spoken. I think one of the saddest things about NYC is that friendships don't last forever here. People tend to bond together during specific times of their life and after that phase has passed, it's very easy for those people to have moved on. This might be a universal thing, but I think it happens more commonly in NYC

Overall, highly recommend NYC.


  • Analyst 1 in S&T - Equities
Feb 16, 2021 - 3:07pm

I've never heard climate cited as a reason to live in Chicago...I also don't really consider it a major city with ~2.xx million residents. 

Feb 16, 2021 - 5:11pm

Although the municipality has ~2.7m, the "Chicago area" has ~10m

Also, NYC (~8m) and LA (~4m) are the only two US cities with populations bigger than Chicago, so even if you're using the city proper as the metric there's no way Chicago isn't a major city

Feb 16, 2021 - 5:12pm

Would need high 7 to 8 figures to live properly in NYC w/ a family. People think that's nuts but go look at a 4 bedroom home in Manhattan and get back to me. 

The number one thing I didn't like about NYC was that I made good money but didn't feel like it and almost felt physically gross living there w/ the high population density, bad infrastructure for its size, bugs, and trash in the streets. 

I think it's pretty telling that of the major global cities, such as NYC, London, Tokyo, HK (pre-2019), and maybe Paris, NYC is a clear last for me. 

But if you are rich enough or don't plan on having kids ever it doesn't matter I guess. 

  • 1
  • Analyst 1 in AM - Equities
Feb 16, 2021 - 6:18pm

Would say that is the transplant perspective as you are probably looking solely at Manhattan. I grew up in Tribeca but have plenty of friends who grew up in Queens and Brooklyn in affordable homes and still had a great time. 


Also would like to add that while this is not chump change, know quite a few people whose combined income is 1.5m-2m (quite reasonable assuming MDs/higher up in finance + consulting) who are able to purchase largish townhomes in Manhattan. But once again as you said, this requires two high earning individuals to accomplish but it is more feasible in this specific community. 

  • Associate 1 in IB-M&A
Feb 20, 2021 - 8:40am
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