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Chicago's rivalry with New York shaped both cities

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New York Rivalry

Katherine Nagasawa

Ask anybody you meet on a Chicago street who the city’s chief rival is, and you’ll almost always hear “New York” (

I've tried this!

). New Yorkers, on the other hand, don’t necessarily think of Chicago as a rival. Curious City recently sent a producer to interview people in midtown Manhattan.

Almost nobody mentioned Chicago and when pressed, one New Yorker scoffed: “I mean, Chicago’s Chicago. You don’t hear much about it.”

This one-sided rivalry may have prompted a question from Curious Citizen Anthony. We say "may have been prompted," because he didn’t share his last name and didn’t return emails. His question: Why does our inferiority complex toward New York exist? When exactly did it start?

I assume Anthony’s referring to Chicagoans’ habit of comparing treasured cultural institutions to New York’s: Deep dish pizza vs. New York style; Second City Theater vs. Saturday Night Live; Cubs vs. Mets (or a half dozen other sports matchups).

You might be thinking: Those are rivalries. Why does Anthony call it an inferiority complex?

Well, interestingly, history shows that Chicago and New York were once rivals in a contest Chicago ultimately lost, and evidence suggests Chicago retains some bitterness about coming in second.

The timeline below tracks Chicago’s growth in the 19th century, a time of expansion when American cities engaged in a great contest for prominence, and kept “score” by tracking population. It chronicles the decades in which New York saw Chicago as its closest rival, explains the origins of the Second City nickname, and reveals how Chicago has settled into it’s self-appointed role as “Number 2.” 

A rivalry, or inferiority complex, may not seem that important to a city’s history or daily life. At most, it might seem to have a psychological impact. But Chicago’s push and pull with New York also helped to physically shape both cities. New York was spurred to annex not only Brooklyn, but parts of Queen’s County, the Bronx and Staten Island that may have never joined the city otherwise. To this day, architects in both cities compete to see which can build the tallest or most impressive buildings.

Without the need to prove its greatness, Chicago may not have enthusiastically adopted the Burnham Plan of 1909, which altered its landscape forever. Going farther back, Chicago’s rivalry with St. Louis, Milwaukee and Cincinnati spurred investment in infrastructure like the canal, the railroads and other industry that helped Chicago become, for better or worse, the Midwest’s largest metropolis.

All of this raises a question: What use could  we put this rivalry to today? Is what Anthony calls “our inferiority complex” at all helpful?  

Barring a tremendous change in current trends, Chicago is out of the running when it comes to population. (Chicago may be passed by Houston soon). When it comes to prominence, Los Angeles and New York with their theater, films, and publishing seem to have an insurmountable lead.

But is there any value in envying these vast, congested metropoli?

If you take stock, as we asked Chicagoans to do, Chicago has its own advantages they wouldn’t trade.

According to them, Chicago is more livable: It’s easier to navigate by car and public transit; Chicago people are friendlier; Chicago’s cuisine is better; Chicago is cleaner. If all of this is true, then Chicagoans are secure in their preference to be Chicagoan. Maybe it’s time to act like it.

Jesse Dukes is a senior podcast producer for WBEZ.

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