New York City vs. Chicago: Which One Is Best?

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If your goal is to visit or live in an exciting city and enjoy the many perks it offers, you cannot beat either New York City or Chicago, but which one should you check out first?

To be sure, both cities are large and offer tons of things to do, which means you have to look at various aspects of each of them and compare them so that they meet your own personal preferences.

Let’s take a look at some of the things most travelers look for when visiting either of these fantastic cities.

Where Would You Rather Live: New York City or Chicago?

New York City vs. Chicago: which one is right for you? Besides research, it’s good to visit each of them in person before deciding to move there permanently.

To get started, below are some aspects that most people consider important when they want to move somewhere else, and what those aspects are like for both of these cities.

Types of Food and Restaurants

We all love to eat, but when it comes to the diversity of its restaurants, both NYC and Chicago have a lot to offer, which means your preferences will help you decide which city is your favorite. In the Windy City, you can find Italian beef, deep-dish pizza, and of course, the famous Chicago hot dogs.

NYC boasts restaurants that offer dishes such as New York pizza, bagels, Chinese dim sum, and yummy New York hot dogs.

The Nightlife

If you’re young and active, the right nightlife is important to you, and again, both of these cities shine in this area. Bars and clubs in Chicago include the Beauty Bar, Smart Bar, and Le Nocturne, while NYC is home to Le Bain, Paul’s Cocktail Lounge, and Avant Gardner.

Even better, in both cities, you can enjoy much of the nightlife enjoying the colorful lights.

Historical Sites, Museums, and More

When in Chicago, look for amazing sites that include the Art Institute of Chicago, Museum of Science and Industry, and Adler Planetarium. Landmarks include the Willis (Sears) Tower, the iconic Cloud Gate (the “bean”), and Buckingham Fountain, to name a few.

In New York City, look for Central Park, the Statue of Liberty, Metropolitan Museum of Art, the Museum of Modern Art, and of course, the Empire State Building. The fact is, when it comes to both museums and historical sites, both cities have too many of each to include in this list.

Shopping Opportunities

Let’s face it, finding places to shop is important regardless of where you live, and both of these cities offer amazing shopping scenes. Chicago is home to an area called the Magnificent Mile and the shops found on the famous Michigan Avenue.

Visitors from all over the world come to shop at places in NYC that include tons of street markets if you’re on a budget and Fifth Avenue if you’re not!

Backpackers and People on a Budget

Naturally, both of these cities can be very expensive to live in, but Chicago might have a slight edge over NYC in this area. Why? Because there are numerous hostels you can stay in that are cheap but nice. NYC, on the other hand, usually has fewer cheap places to stay and can be more expensive to visit or to live in when money is a concern.

When it comes to buying a home, NYC isn’t the place to be when you’re on a budget. Chicago is also expensive, but overall real estate seems to be just a tad more affordable.

Public (Mass) Transit

If you’re going to live in an expensive city, you might as well save yourself the expense of a car if that’s possible. Both Chicago and New York have great mass transit systems, which includes the Chicago “L” subway system, lots of taxicabs, a commuter rail, and lots of buses with convenient routes.

In NYC, you’ll find one of the most extensive public transportation systems in the world – so much so that many New Yorkers never get their driver’s license, or get it later in life. The system includes a great subway system, cabs, buses, and even a convenient ferry system.

Good for Walkers?

For people who love to walk everywhere, deciding between Chicago and NYC can be tough. Because both cities are very congested and have a lot of traffic, people in both of them often choose to walk wherever they need to go instead of trying to drive. This is especially true if you choose to live in the suburbs of either city, where sidewalks are very common.

The Music Scene

If you love music, especially live music, neither Chicago nor NYC will disappoint. When in Chicago, look for facilities that offer excellent blues and gospel music, which you can visit nightly. If you choose New York instead, you can enjoy Radio City Music Hall, Music Hall of Williamsburg, Beacon Theatre, and Forest Hills Stadium.


To be sure, Chicago and New York City are in stiff competition when it comes to culture, conveniences, and things to admire and do. You’ll never be bored in either of these cities, so all you have to do is decide which features are most important to you, and you’ll be able to make the right decision in the end.

Yet another factor to consider is the weather, which can be brutal in both cities. That being said, if you’re used to cold weather and you love living somewhere that offers four seasons, choosing either Chicago or New York City will make you happy.


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