Chicago Architecture Versus New York Architecture

November 9, 2019

Comparing Architecture of Two Prominent American Cities

Take a look at two very large metropolitan areas in the United States, Chicago and New York. They are very different in life style, charm, and architecture, but at the same time are very similar. There are so many different aspects to consider when comparing and contrasting two cities, so pin pointing a certain one makes the job much easier. Allow us to choose architecture as a category to compare because both cities share very similar architectures, but at the same time come off as two whole different types of cities. Check out this post on Chicago vs New York skyline.

There are many other cities that could be compared in the United States in regards to architecture, but Chicago and New York are the only two that actually have rich architectural and design history unlike any other city. Los Angeles, Seattle, Boston, and Philadelphia all are honorable mentions, but they just cannot compete with the Chicago's god-crafted skyline and New York City's amazing WWI architecture.



Chicago: The Windy City

Chicago is known as the "Windy City", "City of Broad Shoulders", and the "Second City". Inhabited in the 1770's by French Explorers, Chicago was found via the Great Lakes System. Lake Michigan only helped the growth of Chicago over the next centuries to come. Unlike New York, Chicago was unheard of in the 1700's due to it simply not being a power house yet. Chicago quickly grew as did its architecture. Most of Chicago's earliest architecture was seen in Cathedrals and Churches due to high rises not being invented yet. Once the first high rise in the United States was built in Chicago, a whole revolution followed. Daniel Burnham and Louis Sullivan were just a few of the most prominent early Chicagoan architects. Today, Chicago is known for the Willis Tower (formerly known as the Sears Tower), John Hancock Building, Trump Tower, and many more amazing modern high rises.



New York City: The City That Never Sleeps

New York City is known worldwide for being arguably the most powerful economic city in the world. Inhabited in 1624, New York City had a great location and group of people who made sure their city was the best. New York City has been through it all when it comes to American architecture simply because it is very old. Some buildings date back to the Revolutionary and Civil Wars. New York prospered during the World War eras due to the construction of its first skyscrapers. The Empire State Building was built in 1931 and was a huge success. It became the tallest building in the world at the time. This gave New York City a much better comparative advantage over large cities nearby such as Philadelphia or Boston. Modern New York City saw a jump in medium to high rise building construction, leading New York to become a urban chaos of building lined streets after streets.


Positives of Chicago and New York City Architectures


  • Chicago's skyline looks like it was crafted by God and is very aesthetically pleasing from most views.
  • Chicago has always had the most tallest buildings in the Top 10, proving that it is very dense in certain areas such as the Loop or Streeterville.
  • Historic buildings such as the original Water Tower Place and the Wrigley Building.


New York City:

  • New York City's World War I and II era skyscrapers are beautiful and extremely historical
  • The sense of urban chaos in the city gives off a great vibe
  • New York City always has a prominent building that shows its power in the United States (World Trade Center, Freedom Tower)


Negatives of Chicago and New York Architectures:


  • Chicago has a little amount of pre-World War era architecture besides cathedrals due to being a younger city and the Great Chicago Fire.

New York City:

  • The city seems to have so many buildings of the same height that it just looks bland when comparing it to a more sculpted Chicago skyline. New York City has more buildings than Chicago, but has less taller ones in the Top 20 in the United States



Chicago Skyline from the north


The beautiful Chrysler Building in New York during the 1940's

Comments by others who have weighed in on the topic:

"As impressive as New York is, I have to give this to Chicago by quite a bit. The most impressive thing about New York is the size and sprawl of buildings, which can only be matched in this world by Hong Kong. While there are definitely some standout skyscrapers in NY, I think that Chicago has a bigger proportion of utter-awe skyscrapers. The older Chicago buildings look a little cleaner than the old New York buildings." ~ Waytooboxy from

"Chicago has certainly been the birthplace of the modern highrise, and has always been the more adventurous of the two.... but New York has a certain "something" that can't be denied. It is just such a
hectic mish-mash of everything that you have to love it." ~ Taller, Better from

"Chicago's three tallest are all from the 1960-'70's, which is bland and boring compared to NY's three tallest, which are all from before WWII. NY, in general, has way more pre-WWII buildings, high-rise and low-rise, than Chicago." ~ A42251 from


More Chicago Photos:

chicago vs new york skyline chicago vs new york skyline

More New York City Photos:

chicago vs new york skyline chicago vs new york skyline chicago vs new york skyline

What do you think about Chicago and New York's Architecture! Who win the battle on this topic, Chicago or New York City? Please leave your comments below in the comment box or on Facebook or Twitter. Also vote on our poll above.

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David Sunnyside
As the co-founder of Urban Splatter, I merge my engineering expertise with digital marketing savvy to offer fresh perspectives on architecture and design. My technical background ensures our content's precision, while my dedication to meditation brings a mindful approach to our bustling digital presence. Join me in exploring the artistry and analytics of building spaces at Urban Splatter.

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10 comments on “Chicago Architecture Versus New York Architecture”

  1. Chicago has a much more fascinating skyline. If you want to have a higher view go to Chicago's Sears tower (AKA Willis tower) It has 110 floors but the world one trade center in NYC only has 104.

  2. I live here and its definitely not parking lots everywhere outside of downtown. There urban neighborhoods. You just didn't look.

  3. From an architectural perspective, Chicago cannot be bested in the US. NYC is an urban jungle. Chicago is an architectural masterpiece. The names associated with the buildings and the sheer beauty of the buildings is more than a match for NYC.

  4. The thing in Chicago is it is just downtown really that has the buildings, if you go a few blocks south of the Sears Tower you run into parking lots, same thing with going north of it, you will see tons of empty lots then you quickly get into suburban style housing with front yards, wide street setbacks, etc. NYC is far far more urban than Chicago, but it's not as obvious until you get down to street level instead of those aerial shots. Even Atlanta has an impressive skyline but it looks terrible from the ground.

  5. I´m very exiting what I will see there in Chicago when I will be there. I´m sure it will be 100% US American style and it will be so awesome.

    Greetings from Germany

  6. Correction: the Sears Tower is now named the Willis Tower. Chicago does also now have the Trump Building. Brownstones are very characteristic to New York. It is so hard to actually decide between the two powerhouses of the best and most dynamic styles of architecture. I would just say Chicago because that where I am from!

  7. The comparison is perhaps invidious; the suave monumentality of the Chicago Loop, a unified architectonic organism, is nonetheless equalled by the sheer immensity of vertical fabric in Midtown Manhattan. As far as individual buildings are concerned, Chicago's Tribune, Wrigley, Palmolive &c find equivalents in the RCA Victor, Flatiron, Radiator, &c; the Chicago School and Wright's Oak Park are unique but so is NY brownstone; Int'l Modern icons in Chicago incl. Mies's IIT, Federal Ctre & 860-80 Lake Shore Dri while NY has the Seagram & SOM's Lever, Pepsi-Cola & Mfg Trust Co. Bank - and on its goes. Generally, Chicago is more resolute, disciplined and, ultimately, sublime, but NYC has the overpowering force of numbers. The beacons: Sears & J Hancock vs. Empire State & Chrysler - how to choose?

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