Chicago or New York: Which City Comes Out on Top?

Whether it’s for a big city break or a place to live, many people wonder if they should go to Chicago or New York. If that’s your dilemma, I’ve written this guide to help you decide. 

I was brought up in Chicago, so I know the city better than anywhere. As for New York, I’ve visited at least five times for both business and pleasure, meaning I’ve spent a fair bit of time there. 

If you’re weighing up Chicago vs New York city, read on so I can help you decide! 

Chicago or New York, how to decide? 

The first factor to consider when choosing between New York and Chicago is – why do you want to go to one or the other?

Are you trying to figure out where to travel for a few days, or want to stay a little longer? Or perhaps you’re even thinking about relocating to one of the largest cities in the US?

New York is perhaps the more obvious choice. It’s not only bigger, but also better known on a global scale. Most travelers want to see the Big Apple at least once in a lifetime.

The most common places people from outside of the US want to go to are New York and LA, and the same applies to Americans living in other states.

I was born in Chicago, and have so far spent a significant part of my young adult life living and working in the city. So I’ll freely admit to having a bit of built-in bias.

But I’ve also met many other folk from elsewhere who agree that Chicago is a really great place to be. For those reasons, I often advocate to those people I meet on my travels to not overlook Chicago in favor of NY (or LA).

In this post I’ll break down your decision by taking a look at the weather, crime levels, food, cleanliness, population and size, plus the cost of living in each city.

Next, we’ll take a look at why each city might be right for you, before wrapping up with my final verdict. Read on!

Chicago vs. New York

Why are factors like food, size, the weather, cleanliness, crime levels, and the cost of living important?

Well they’re going to determine exactly how you’ll experience each city in terms of safety, dining out, what you can do there in terms of seasons and your budget, and more.

Things like the size and cleanliness of the city might also have a big impact on how much you enjoy spending time there. 

Is crime higher in NYC or Chicago? 

According to Numbeo, crime levels are higher in Chicago than in New York City.

At the time of writing (March 2025), the latest updated figures from February and March 2025 show the level of crime as 78.58 in Chicago, as compared to 55.04 in New York. 

Using these figures, the level of crime in each city is classed by Numbeo as high in Chicago and moderate in New York. 

Both cities are rated as high when it comes to increasing crime levels over the last three years. 

When it comes to walking around alone, Chicago is classed as moderately safe by day, while New York is given a ‘high’ rating. Safety levels when walking alone at night are low in Chicago, as opposed to moderate in New York.

So on the surface, it seems that New York is the safer of the two cities. However, as with any place on the planet, crime levels vary a lot depending on the neighborhood.

Personally, I feel safer in Chicago. But, this is also the city I’m most familiar and comfortable with so that may be why.

Winner: New York | Score: Chicago 0 New York 1

Which city is cleaner, Chicago or New York?

I’ve experienced Chicago to be cleaner than New York, and I’ve heard others say the same. Overall, a quick search reveals that people on sites like Quora and Reddit tend to agree that Chicago is cleaner than New York. 

So why is Chicago cleaner? It’s in the way the city is managed, and the local government’s commitment to cleanliness as well as beautification. This means the streets are swept and the trash is collected more often. 

New York is also more densely populated, which creates more dirt and trash per square meter or mile. 

Chicago’s alleys also provide a place for trash to be stored out of plain sight, whereas in New York it’s left out on the curb for everyone to see. 

Winner: Chicago | Score: Chicago 1 New York 1

Chicago vs NYC population 

When it comes to the Chicago vs New York question, this is one of the biggest differences. While exact figures vary according to the source used, New York is home to around 8.1 million people. 

Chicago, by contrast, has about 2.7 million residents. This means its population is only around a third of New York’s. 

According to Choose Chicago, the city covers 234 square miles. Britannica states that New York comprises around 305 square miles. This means that while New York is bigger by area, it’s far more densely populated than Chicago. 

Add tourist numbers to the permanent population and you get an even clearer picture. New York’s Office of the Mayor says that the city gets about 65 million visitors per year, while Choose Chicago says around 50 million people stay there each year. 

So New York is busier in terms of tourism, adding to its existing population density per square mile. This makes Chicago a more peaceful place to be.

I’ve felt this for myself. After returning from a few days in New York, Chicago feels spacious and like a breath of fresh air. It just feels like there’s more room here to comfortable move around.

Winner: Chicago | Score: Chicago 2 New York 1

Who has better food, Chicago or New York? 

Whether New York or Chicago has better food is a very subjective matter indeed. Everyone will have a different opinion! So it really depends on what you personally like to eat. As well as how much you want to spend on food, maybe. 

New York is famous for both its fine dining restaurants, and the fact that you can get cuisine from anywhere in the world there. 

In culinary terms, Chicago’s deep dish pizza and hot dogs are what the place is best known for on the surface. The city’s proximity to so many Illinois farms is also great news for any fans of farm-to-fork dining. 

Then the matter of Chicago style pizza vs New York pizza can be a big debate in its own right. Again, everyone has their own opinions.

But beyond that, Chicago also has a pretty spectacular fine dining scene of its own. With diverse influences across its many neighborhoods, here too, you’ll find cuisine from around the world. 

If you want a high variety of food available at all hours of the night, it’s got to be New York. The sheer volume of eateries alone means you’ll never run out of somewhere new to try. 

But the number of restaurants aside, both cities offer a melting pot of food across a variety of price points. This one’s a tie.

Winner: A tie | Score: Chicago 3 New York 2

What’s the weather like in Chicago vs New York? 

Chicago is generally slightly cooler than New York, whether you look at it month-by-month or on a seasonal basis. The hottest month in both cities is July, when average daily maximum temperatures can reach 82°F (28°C) in Chicago and 86°F (30°C) in New York. 

At the other end of the scale, daily highs in January are around 32°F (0°C) in Chicago and 39°F (4°C) in New York. This is the coldest month in both cities.

It’s a similar picture for the rest of the year, with just a few degrees’ difference on average between the two cities. 

Chicago is drier than New York, though. There are six days of rain per month on average throughout the year in Chicago, as compared to seven to eight in New York. 

However you can generally expect more wind in Chicago, hence one reason for the Windy City nickname!

Winner: A tie | Score: Chicago 4 New York 3

Related reading: How to Build Your Winter Travel Capsule Wardrobe

Is the cost of living better in Chicago or New York? 

As you might expect, Chicago offers lower living costs than New York City.

According to Numbeo, New York is 22.4% more expensive than London, while Chicago is 9.5% less expensive than the UK capital. Which is a considerable difference.

This means your money will go further in Chicago. From meals or drinks out and grocery shopping to transport tickets, just about everything is more affordable, meaning your budget can more readily be stretched. 

In reality, you’ll have more to spend on experiences, luxuries, and gifts and souvenirs in Chicago than you would in New York. 

Winner: Chicago | Score: Chicago 5 New York 3

Chicago vs New York City – which one is right for you? 

An important consideration I’ve not touched on yet is what you’re actually into. What you want to do is key when deciding on New York or Chicago. Here are some summaries of what the first and third most populous cities in the US have to offer. 

Chicago is for you if…

In 2024, Conde Nast Traveler named Chicago as the best big US city “yet again.” The reasons cited included world-class museums, attractive architecture, and thriving foodie and brewing scenes.

Chicago’s outdoor areas are also unbeatable, and include the lakefront, the parks, and even Wrigley Field. Lake Michigan is always there when you crave time by or on the water. 

The experts added that you’d need to return a number of times to see everything you’ll want to, from downtown to over 75 neighborhoods just waiting to be discovered.

Each is filled with friendly people, atmospheric bars, and restaurants serving top-quality food.

The fact that Chicago is also more spacious than New York leads to a more chilled-out vibe, too, which is appealing whether you want to pay the city a short visit or actually live here.

In short, Chicago is relatively cheap, less crowded than NYC, and cleaner too. 

The main downside is that Chicago does have higher crime rates than New York, but if you choose your neighborhood carefully and exercise common sense, then your chances of becoming a victim of crime can easily be minimized. 

NYC is for you if… 

New York City is seen as one that belongs on everyone’s bucket list. It’s bright, bold, and sometimes brash – and many parts are also beautiful. Of course the Big Apple offers some of the best hotels, restaurants, museums, galleries and shops in the US.

The biggest attractions include Brooklyn Bridge, Central Park, the Empire State Building, the Statue of Liberty, and of course Times Square. Even Grand Central station is a very familiar sight to most people.

People from all over the world regard spending time in NY as a rite of passage, and many want to call the city home, at least for a while.

It’s known as a great place for building careers and connections, and the opportunities for creators are seen as second-to-none.

With such a high population, there are more people to meet and contacts to be made, which may lead to superior opportunities.

 All this comes at a price, however, with soaring rents in exchange for very little space. 

Final Verdict: Chicago or New York? 

At the outset, you might have expected an article written by a Chicagoan to come down on the side of the Chi-Town.

As opposed to the City That Never Sleeps. And indeed Chicago did score higher than New York in the categories I used to decide which might be best for you.

According to the criteria I used, New York was a winner in terms of lower crime levels, while Chicago came out on top for cleanliness, fewer crowds, and the cost of living. The cities tied when considering the weather and the food scenes. 

But you know what? Other criteria could also be used to settle the New York vs Chicago debate. It all comes down to individual choice. Where do you really want to spend your time, and what do you want to see and do the most? 

If you really can’t make up your mind, maybe you should just go wherever your gut instinct dictates. Ideally, though, do visit both cities at least once during your lifetime.