Chicago is called the Second City for a few commonly cited reasons: it was rebuilt after the Great Chicago Fire, it was once the second-largest city in the United States, and it has long been compared with New York City. Over time, the nickname has become less of an insult and more of a reflection of Chicago’s resilience, reinvention, and civic pride.

Chicago has many famous nicknames, including The Windy City, Chi-Town, and The City of Big Shoulders. But the Second City nickname has one of the most interesting histories because its meaning has changed over time. What started as a comparison to other cities has become part of how Chicago tells its own story.

If you’re planning a Chicago sightseeing itinerary or looking for things to do in Chicago, understanding the city’s nicknames is a useful way to learn what makes Chicago unique. These Chicago facts also help explain the city’s architecture, neighborhoods, culture, and sense of identity.

Quick answer: Chicago is known as the Second City because it was rebuilt after the Great Chicago Fire, was once the second-largest city in the U.S., and has often been compared to New York City. Today, the nickname reflects Chicago’s resilience, reinvention, and civic pride.

Want to experience the Second City from above? Visit Skydeck Chicago on the 103rd floor of Willis Tower for sweeping views of the skyline, neighborhoods, lakefront, and landmarks that define the city.

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The Main Reasons Behind Chicago’s “Second City” Nickname

Chicago’s Second City nickname does not have just one accepted origin. Several commonly cited explanations point to different parts of the city’s history, from rebuilding after disaster to competing with other major American cities.

The Great Chicago Fire: One explanation connects the nickname to the city’s rebirth after the Great Chicago Fire of 1871. The fire destroyed a large portion of the city, giving Chicago the chance to rebuild with stronger materials, new infrastructure, and more thoughtful urban design. According to this theory, Chicago became a “second” city because it was built twice.

Rivalry with New York City: Another explanation comes from Chicago’s long-running comparison with New York City. In the early 20th century, Chicago was growing quickly and competing for influence as a major American metropolis. Writer A.J. Liebling helped popularize the phrase in his book Chicago: The Second City, using it as a sharp comparison to New York.

Former second-largest city status: Chicago was also once the second-largest city in the United States by population, behind New York City. That ranking added another layer to the nickname and reinforced Chicago’s place as one of the country’s most important urban centers.

What Does “Second City” Mean?

Second City means Chicago, but the meaning of the nickname has changed over time. In some uses, it referred to Chicago being second to New York in size, influence, or cultural status. In another interpretation, it refers to Chicago being rebuilt after the Great Chicago Fire.

Today, the Second City nickname is often understood more positively. Rather than suggesting Chicago is second-best, it reflects the city’s ability to rebuild, adapt, and define itself through architecture, industry, culture, food, sports, music, comedy, and neighborhood identity.

That spirit is part of what Chicago is known for and one reason the city remains such a memorable destination for visitors.

Is Chicago’s “Second City” Nickname Related to The Second City Comedy Club?

Chicago’s Second City nickname came before the famous comedy institution. In 1959, the improv comedy group The Second City adopted the name with a self-deprecating nod to Chicago’s nickname.

The name proved fitting. The Second City became one of the most influential comedy institutions in the country, helping launch the careers of performers including Bill Murray, John Candy, Steve Carell, Tina Fey, Amy Poehler, and many others.

Today, The Second City remains an important part of Chicago’s entertainment scene, but the city’s Second City nickname has a broader history tied to rebuilding, rivalry, population, and civic identity.

What Other Nicknames Does Chicago Have?

The Second City is only one of several well-known Chicago nicknames. Each nickname highlights a different side of the city.

  • The Windy City, one of Chicago’s most famous nicknames
  • Chi-Town, a casual nickname often used in pop culture and everyday conversation
  • The City of Big Shoulders, a phrase from Carl Sandburg’s poem Chicago that reflects the city’s working spirit
  • The Second City, a nickname tied to Chicago’s rebuilding, rankings, rivalry, and resilience

Together, these nicknames show how Chicago has been defined by history, hard work, creativity, and reinvention.

Experience Chicago’s Second City Story from Skydeck

After learning why Chicago is called the Second City, Skydeck Chicago gives visitors a way to see the city’s history, architecture, neighborhoods, and skyline from one of its most iconic vantage points. Located on the 103rd floor of Willis Tower, Skydeck offers a clear view of the city that rebuilt, grew, and earned its place among America’s great urban destinations.

For first-time visitors, Skydeck Chicago is a useful starting point for understanding the city’s layout. From above, guests can see the Chicago River, Lake Michigan, downtown architecture, surrounding neighborhoods, and the skyline that helps make Chicago instantly recognizable.

Skydeck also offers more than skyline views. The experience includes an interactive Chicago Museum that explores the city’s history, architecture, sports, pop culture, food, music, and people. It is a natural stop for visitors who want to understand what makes the Second City such a distinctive place.

See the Second City from 1,353 feet up. Book your Skydeck visit today!

Frequently Asked Questions About Chicago’s Second City Nickname

Why is Chicago called the Second City?

Chicago is called the Second City for several reasons. The nickname is often connected to Chicago being rebuilt after the Great Chicago Fire, once being the second-largest city in the United States, and historically being compared with New York City.

What does Second City mean?

Second City is a nickname for Chicago. It can refer to the city being rebuilt after the Great Chicago Fire, its former ranking as the second-largest U.S. city, or its long-standing comparison with New York City.

What city is known as the Second City?

Chicago is the U.S. city most commonly known as the Second City. The nickname is part of the city’s history and cultural identity.

Is the Second City nickname about Chicago being rebuilt?

One common explanation says Chicago is called the Second City because it was rebuilt after the Great Chicago Fire of 1871. In that interpretation, Chicago became a second version of itself after the fire.

Is Chicago’s Second City nickname related to The Second City comedy club?

The city’s nickname came first. The Second City comedy group adopted the name in 1959 as a reference to Chicago’s nickname and became one of the most influential comedy institutions in the country.

What are other nicknames for Chicago?

Other Chicago nicknames include the Windy City, Chi-Town, and the City of Big Shoulders. Each nickname reflects a different part of Chicago’s history, culture, or public identity.