Do you prefer New York City or Chicago? It Is a frequent question that people ask when thinking of travel or moving. Although it might sound like an easy-peasy question, it is a tricky one to give an answer to. It is difficult to give one and correct answer to this inquiry because both Chicago and New York have their own distinct features. How would you even compare two different cities? What criteria should you use?

Those factors will be different depending on your goal. For the tourists from Europe who are planning a city trip to one of the US metropolises, those are one set of criteria. However, for the movers who want to change their residency place and who can be moving from another US city they would be completely different. The tourists who often do not have a lot of time on their hands and quite restricted nonstop flight choice to the United States from Europe, should look at the tourists attractions. They should choose between New York City, Chicago or Washington because it is impossible to visit all those cities in a couple of days and have quality time there. So we have come up with some overview of what New York and Chicago can offer. We will talk here not only about sightseeing options but also other criteria which might be even shocking and not always positive. Our idea was not to create yet another city guide but propose an alternative view. For those who are moving home we highly suggest to check this moving address change checklist to avoid many problems which are likely to occur after the move. 

Let's start with some geographical facts namely size, location and structure.


New York City is situated in the New York state which stretches on the East coast of the United States. It might sound like a Wikipedia entry but those are just facts. NYC is home to more than 8 million people. Imagine this city occupied approximately by the whole Austrian population. Just imagine, the same number of people as in the whole country. It is pretty impressive as the density of the population in NYC is really astonishing. But it's not only the population and its density that are impressive, the size of the city itself is pretty striking too. Frequently when people talk about the name New York, they only think of Manhattan. Of course, Manhattan is featured on most tourist magnets depicting its famous skyline, buildings, and sights. Yet NYC is much more than only Manhattan and it also includes hip Brooklyn, hot and diverse Queens, the Bronx, and Staten Island. All those parts have different reputations and often people find the Bronx quite repugnant given its renome. They are afraid to go to the Bronx and to get into the middle of a gang war, or even worse to be robbed and shot dead. The reputation of this district can be actually exaggerated so it is uneasy to say how the Bronx actually is. Is it as dangerous as its image makes it look? Perhaps not but we won`t dive into too much detail to check upon those rumors about the Bronx. 

Chicago is situated relatively close to New York. The key word here is of course relatively as there are almost 800 miles separating them. Chicago lies in the Illinois state and makes part of the Midwestern United States. When it comes to Chicago's population, it is home to some 2,7 million people. On the first sight it might seem that Chicago is a tiny town or even a village as compared to New York City. However, Chicago is part of the Chicago metropolitan area which has almost 10 million residents. What's really great about Chicago is that it is situated on the bank of Lake Michigan. Thanks to its location Chicago has amazing holiday air, at least from April to October when the weather contributes to the warm and relaxed atmosphere. Just as NYC, Chicago includes different localities for example Wicker Park and Logan Square have a reputation of hipster areas, the Loop is attractions` hub, and the Gold Coast is a luxurious district. You might wonder if there is some equivalent repugnant district in Chicago like the Bronx? It is worth stating that Chicago's crime rates are much higher than those of New York. Englewood, Auburn Gresham, Fuller Park, and Riverdale are the neighborhoods notoriously known for their high crime rates and low incomes.

As you can see NYC and Chicago are quite similar in this regard. Both are situated by the water and have multifaceted districts, fancy, hippy, and repugnant. The flight time from Europe is more or less the same to both cities. NYC and Chicago each get a point, so point 1-1.

What are their nicknames?

At first sight, there is no big deal with the nicknames. And yet once they stick to some places, it seems they do so forever. In the case of New York, it is widely known as The Big Apple. Next to that it is referred to as The Capital of the World and The Center of the Universe. While those names sound rather snobbish, it’s another nickname - The City That Never Sleeps - seems to match New York perfectly well! On the other hand, Chicago is known under the nicknames like The Windy City, The City of Big Shoulders, The City That Works, and The Second City. They are all straightforward and cool. So in the nickname category Chicago gets the point and makes it 2-1.

What are their skylines?

Certainly, a skyline is something that marks each city and makes it unique as it features an ensemble of the main historical sights. Most probably you have heard people saying „The skyline of …. is incredible” ... Think of Paris, Rome, Antwerp, Vienna…  And New York can also be in this row because it is hard to imagine somebody not being astonished by its skyline seen in the direction of Manhattan. No matter how many times you have seen it, this skyline remains alluring and offers an unbelievable view. We definitely recommend checking out the following places to enjoy New York`s skyline as Brooklyn Bridge Park with its wooden posts from an old wharf and Gantry State Park by the original Pepsi symbol. Admittedly, Chicago also offers a stunning skyline. The optimal viewpoints would be then the classic spot at Adler Planetarium from where you’ve got a great view of the city with the lake in the foreground or the Bean in Millennium Park. Here the wooden post and old pier outweigh, so New York gets another point, so it becomes 2-2.

 What are their architectural treasures?

We don`t know whether you guys are into architecture or not, but we adore it. And from this point of view both New York City and Chicago are worth visiting as they offer wonderful design of buildings. It is difficult to say which of them has the most remarkable constructions. The features of New York City are undoubtedly the Empire State Building, the Flatiron, and the Chrysler. They all look good on pictures, right? Additionally, the New York Public Library, the Grand Central Terminal, and the Guggenheim Museum look fantastic too. Last but not least, we are true fans of the bridges in New York, in particular about the construction and design of Manhattan and Brooklyn Bridge.

Chicago is home to the famous masterpieces such as the Wrigley, the Carbide & Carbon or the Rookery Building. What we like too, is the Aqua Tower which is decorated with ornate concrete balconies that look like foaming waves. It's up to you whether you could name Marina City appealing but it is certainly remarkable. On the top of that the Cultural Center has outstanding interior design. And while Chicago has a lot of architectural wonders to boast with, it won't overtake New York. Well, at least for us, as we simply love the NYC bridges. So here it is 2-3.

What are their famous parks?

New York as well as Chicago are proud of their distinguished green oases amidst the city. New York has its Central Park while Chicago has the Millennium Park which is attached to Grant Park. Central Park is a space of genuine recreation and the green lung of NYC whereas Millennium Park is one of the major tourist sites with numerous attractions and offering lots of activities. The area of Central Park is approximately 35 times bigger than that of Millennium Park. Central Park attracts not only tourists but also the locals. What we like about those parks are probably their bridges namely the Bow Bridge in Central Park and the BP Pedestrian Bridge in Millennium Park. Of course, we find Millennium Park with its renowned Cloud Gate really enjoyable, Central Park overshadows it with its distinct park feeling with all the stunning ponds and lakes. Therefore, it is 2:4 for New York.

And what about their ambience?

This is a tricky question and the answers can depend on the day, mood, and even neighborhood you walk around. In general, Chicago has a much more relaxed atmosphere. The locals do not rush through the streets, not even in the financial district The Loop. As opposed to that, Manhattan exemplifies hurry and reminds constant rush hour. It looks like everybody is guided with the motto the faster the better, regardless of the red lights. Walk on and carry your cup of coffee in your hand and perhaps drink it (or enjoy it?) as you go. But this permanent move has something in it too. We enjoy both chillaxing Chicago and busy New York, so one point to each of them. 3-5.

And what's about music?

Needless to say that both cities gave lots of inspiration for musicians who reflected New York and Chicago in their songs. Among those songs, we shortlisted 3 songs for each city. Again, here it is the matter of taste, but in our humble opinion New York is referred to in more recognized ones. Most people will come up with some New York`s songs if asked about that.  And if asked about the song of Chicago, you might need to reflect a bit, don`t you? We had to look up those songs ourselves too. So here again New York leads. Thus 3-6.

New York

New York, New York by Frank Sinatra (of course, the song of NYC)
Empire State of Mind by Alicia Keys and Jay-Z 
No Sleep Till Brooklyn by Beastie Boys


Tonight, Tonight by Smashing Pumpkins
Homecoming by Kanye West
My Kind of Town (Chicago Is) by Frank Sinatra

We tried to remain neutral in our assessment but judging from the score you might conclude that we are biased towards New York City. However, we actually like both cities, even though it is difficult to get enough of NYC. New York has always something new you can explore. If you haven't been to Chicago yet but have seen NYC, then go for Chicago we'd say. But it's up to you what destination becomes your next pick.