Is Chicago Better Than New York?

Many Midwesterners, like my husband, Joe, and other cosmopolitan individuals, claim that Chicago is better than New York. That “toddlin’ town” is easier to get around, cleaner, and its residents are friendlier, compared to those demonic New Yorkers.

At the Bean (July 2023)

Joe last shared this view when he and I were walking on Michigan Avenue in late August. As someone who once lived in New York and visits there often, my first instinct was to bristle and defend Gotham.

I thought of the lyric from Hamilton about “how lucky we are to be alive right now in the greatest city in the world.” The Schuyler sisters weren’t singing Chicago’s praises in that catchy showtune. 

Chicago may have been Frank Sinatra's kind of town, but he never sang that if you can make it there, you’ll make it anywhere. 

Rockefeller Center Tree
(December 2021)

And "Christmastime in the city" evokes New York, not Chicago.

I have treasured memories of both New York and Chicago. My father introduced me to each city when I was very young. But to say “Chicago is better than New York” is fallacious. Like my dad, I'll take Manhattan. 

The reason Chicago is easier to navigate is that it only has two streets worth walking on: Michigan Avenue and Oak Street.

Moreover, New Yorkers aren't rude. Efficiently brisk? Certainly. In a rush? Yes, but so am I. Opinionated and passionate? Absolutely. But rude? Never! I have seen New Yorkers stop what they were doing to patiently explain to a tourist how to get to Times Square or where to find a good slice. (And a New York slice beats any Chicago deep-dish pie, including Pequod’s.)

Outside Sweeney Todd
(December 2023)

Then there is the matter of culture.

As a theater enthusiast, I appreciate Chicago’s Steppenwolf Theatre, The Goodman, and, for improv, the aptly named Second City—though if you've seen one improv show, you've seen them all. These assets don’t compare to the vibrant, expansive theater scene in New York. To wit, there were three concurrent Sondheim revivals on Broadway in 2023. 

At the Art Institute (August 2025)

One thing I will say about Chicago’s cultural landscape: its Art Institute has more iconic works—both American and European—than the Metropolitan Museum of Art. The Met might have John Singer Sargent’s "Portrait of Madame X," the Temple of Dendur, and some Monet water lilies. But the Art Institute features "American Gothic," "Sunday Afternoon on the Island of La Grande Jatte," "Nighthawks," emblematic Picassos, canonical Monets, and countless other instantly recognizable works. 

Three Midwesterners in Chicago

Two more things.

For shoppers like Joe and me, Madison Avenue and Soho have more bountiful rewards than Oak Street and Michigan Avenue. 

At one of the gazillions
of Chicago steakhouses

And the food: Chicago is known for the aforementioned deep-dish pizza, those Italian beef sandwiches on The Bear, and its 1,734 steakhouses. (That is a lowball estimate; I did not make up that number.) 

Steakhouses are ok, but how many do you need? You can find steaks (and deep-dish pizza and meat sandwiches) and more—from ethnic to haute cuisine to the newest gastronomic trends—in New York.

Comparing cities is, of course, folly. I expect to take many more trips to both New York and Chicago while living in what is truly the greatest city in the world: Cleveland.

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