Why Is Chicago Called the Second City
The real origin of Chicago's Second City nickname, the three competing stories behind it, and how the name lives on in the city's comedy scene and everyday vocabulary.
Why Is Chicago Called the Second City
Chicago is called the Second City for three stacked reasons: the city rebuilt itself from scratch after the Great Fire, it spent more than a century as America's second-largest city behind New York, and a famous comedy theater later adopted the nickname as its own name. Most sites credit just one of these, usually the wrong one first. The fire story is the oldest, the population story is the one Chicagoans actually argued about, and the comedy club is the reason tourists ask the question today.
The nickname has layers, and peeling them in order matters. Chicago did not adopt the name in a single moment or accept it from a single critic. It accumulated, the way city nicknames do, and each layer belongs to a different era: the rebuilding years after the fire destroyed the downtown, the long demographic stretch when Chicago genuinely was the second city of the United States by population, and finally the theater that borrowed the phrase and exported it to the world through generations of comedians.
That last layer is the one that confuses people. When a visitor hears "Second City" today, the first thing that comes to mind is often the comedy stage, not the city. But the theater named itself after the city, not the other way around, and the joke only lands if you already know the nickname was an old insult the city decided to wear as a badge.
What Is the Second City in Chicago
"The Second City" is a nickname for Chicago itself, not a district or a separate place, and it refers to the whole city. The one physical thing in Chicago called the Second City is the comedy theater of that name in Old Town, which took its name from the city's existing nickname. So the answer depends on context: in a conversation about cities, the Second City is Chicago. In a conversation about tonight's plans, the Second City is a comedy venue on North Wells Street.
The theater is the concrete landmark, and it is the reason the question gets asked so often. Tourists hear the phrase, assume it must point to a neighborhood the way the Magnificent Mile or the Loop do, and go looking for it on a map. There is nothing to find, because the nickname was never geographic. It was comparative: Chicago measured against New York.
The venue itself is worth a visit regardless of the etymology. It is one of the most influential comedy stages in the English-speaking world, and alumni rosters read like a history of American television comedy. This site covers the theater and the broader comedy scene in detail on its Second City and Chicago comedy guide, including what a show costs and how to book, since comedy tickets are not sold through this site. The surrounding Old Town neighborhood is walkable and sits a short ride from the Loop on the CTA, where a train fare is $2.50 per the CTA fare table.
The nickname also collides with another Chicago phrase that trips up outsiders. "The Second City" the theater and "the second city" the nickname share a name with Chicago's other famous self-description, and this site keeps them on separate pages for a reason. If you are planning a trip around the name, the architecture is the better target: the buildings Chicago rebuilt after the fire are exactly what the river cruises show off today, and the architecture boat tour guide compares every operator, departure point and price on the water.
Is the Second City Nickname an Insult or a Compliment?
It began as an insult and became a compliment, which is the most Chicago turn of events imaginable. The phrase mocked the city for living in New York's shadow, and Chicagoans responded by using it proudly, the way the city reclaimed other jabs thrown at it over the years. By the time the comedy theater took the name, the sting was gone entirely. Today the nickname is used almost exclusively with affection, and most people who say it have no idea it was ever a slur.
The three origin stories stack rather than compete, and keeping them straight is the difference between a correct answer and the confident wrong one most sites publish.
| Origin story | What it claims | How well it holds up |
|---|---|---|
| The fire and rebuilding | Chicago is the "second" city because the first one burned down and had to be rebuilt | The oldest use of the phrase; the fire destroyed the downtown core and the city rebuilt rapidly on the same ground |
| Population rank | Chicago was the second-largest US city behind New York for roughly a century | The most literal reading; Chicago held second place in the national census counts for generations before being passed by Los Angeles |
| New York's condescension | East Coast writers used it to put the upstart city in its place | The insult layer; the phrase carried a sneer that Chicagoans inverted into pride |
The fire story is the one people love, because it is the most dramatic: a city destroyed and rebuilt, a first version of Chicago lost and a second one raised in its place. The rebuilding was real, and it shaped the skyline visitors come to see. The population story is the least romantic but the most durable, since for the better part of a century the census tables genuinely listed Chicago second, and everyone in the country knew which city was first. The sneer is the layer that turned the whole thing into an identity.
Chicagoans turning an insult into a nickname is not an isolated case. The city has a long habit of absorbing outside mockery and wearing it, and the Second City is the cleanest example. A visitor who understands this understands half of Chicago's civic personality: a city that spent its early decades being underestimated by the East Coast and responded by building bigger, faster and louder than the places doing the underestimating.
How Does the Second City Name Show Up in Chicago Today?
The name survives in three visible places: the comedy theater in Old Town, the city's own tourism and branding vocabulary, and the everyday speech of Chicagoans, who use it with a shrug of pride rather than resentment. You will also run into it constantly in local business names, from bars to tour companies to a famously associated pizza chain style, because a two-word nickname that everyone recognizes is marketing gold. The insult is long dead; the brand is very much alive.
The theater is the flagship. It stages revues most nights of the week, it has trained generations of household-name comedians, and it sits in a neighborhood that makes an easy evening out of dinner and a show. Tickets for comedy are not sold through this site, so check the venue's own box office for current prices and availability, and treat the show as something to book directly rather than through a tour platform.
Beyond the stage, the phrase shows up wherever the city sells itself. Local media use it in headlines, businesses bake it into their names, and tour guides deploy it within the first five minutes of nearly every downtown walking tour. The architecture cruise narrators lean on it constantly, because the rebuilt skyline is the physical evidence for the fire story, and the Classic Architecture River Cruise run by Shoreline Sightseeing spends its full hour to ninety minutes floating past exactly the buildings that made Chicago confident enough to laugh at the nickname. That cruise carries a 4.8 rating across 16,963 reviews, departs from the river's downtown docks, and is the single best pairing with this particular history lesson, since you can see the second city while someone explains how it got built.
The name also does quiet work in how the city compares itself to others. Chicago's rivalry with New York is the subtext of the nickname, and it runs through everything from the pizza wars to the skyscraper race. This site has a full Chicago versus New York comparison if you want to follow that thread, and a guide to the Loop for the downtown core where most of the rebuilding happened. For a deeper cut into the city's criminal-history mythology, which is where a lot of the "second city, first in nerve" attitude comes from, see the ghost and gangster tours guide.
There is a practical takeaway for visitors, too. The nickname tells you where to point your camera. The architecture that made Chicago the second city, the towers raised on burned ground, is concentrated along the river and the lakefront, and the observation decks trade on it: the Skydeck at Willis Tower, once the Sears Tower, and 360 Chicago in the building once called the John Hancock Center both sell the view that settled the argument. If the nickname makes you want to see what the second city actually built, the river and the decks are where you look.
Common Questions About the Second City Nickname
why is chicago called the second city
Chicago is called the Second City for three stacked reasons: the city rebuilt itself after the Great Fire destroyed the downtown, it ranked as America's second-largest city behind New York for roughly a century, and a famous comedy theater later adopted the nickname as its own name. The phrase started as an East Coast insult about living in New York's shadow and Chicagoans reclaimed it as a badge of pride.
what is the second city in chicago
The Second City is a nickname for Chicago as a whole, not a neighborhood or district. The one physical place in Chicago called the Second City is the comedy theater of that name in Old Town, which took its name from the city's existing nickname. In conversation about cities, the Second City means Chicago; in conversation about tonight's plans, it means a comedy venue on North Wells Street.
Is the Second City nickname an insult?
It began as one. The phrase was used to put Chicago below New York, and the city responded by wearing it proudly. By the time the comedy theater adopted the name, the sting was gone, and today the nickname is used almost entirely with affection. Most people who say it now have no idea it was ever meant as a jab.
Is the Second City comedy club named after Chicago?
Yes. The theater in Old Town named itself after the city's existing nickname, not the reverse. It is one of the most influential comedy stages in the English-speaking world, and it is the reason many visitors first encounter the phrase. Comedy tickets are not sold through this site, so check the venue's own box office for prices and availability.
Where should you go to see the "second city" that got built?
The Chicago River and the lakefront. The downtown skyline is the physical evidence for the rebuilding story behind the nickname, and the architecture river cruises narrate it building by building. The observation decks at Willis Tower and 360 Chicago sell the same view from above, and the Classic Architecture River Cruise pairs best with the history.
If the nickname has done its job, it has made you curious about what Chicago actually built, and Best Things to Do in Chicago covers the rest: the decks, the cruises, the museums and the neighborhoods that made a city mocked as second worth a first visit.