Why Is Chicago Called the “Second City”?

Chicago is called the “Second City” due to a combination of historical and cultural factors, primarily stemming from its rivalry with New York City and the name of a book by A.J. Liebling, who coined the term in the 1950s.

In the late 19th and early 20th centuries, Chicago was in fierce competition with New York City. This rivalry was not just about size but also about cultural and economic influence. Chicago was rapidly growing and was, from 1890 to 1982, the second-largest city in the United States. This competition was highlighted during the 1890s when Chicago aggressively campaigned to host the World’s Columbian Exposition, succeeding over New York and St. Louis. This event showcased Chicago’s ambition and its desire to be seen as a major player on the national stage.

The term “Second City” was popularized by New York writer A.J. Liebling in his 1952 book Chicago: The Second City. Liebling’s essays critiqued Chicago’s attempts to rival New York, often portraying it as a city trying to catch up. His writings suggested that Chicago was always in the shadow of New York, both culturally and economically. Despite the somewhat derogatory tone, the nickname stuck and became a part of Chicago’s identity. It was adopted by the famous Second City comedy troupe, which has been a launchpad for famous comedians.

“Second City” is far from Chicago’s only nickname, however. It is called the “Windy City” more for its politics than its climate. Carl Sandburg called it “the city of big shoulders.” In the 1920s, it was a “toddlin’ town” and years later Frank Sinatra would croon “my kind of town, Chicago is.”

Finally, it seems worth noting that the “Second City” is actually now the “Third City,” behind New York and Los Angeles in total population.