Chicago, often called the “Windy City,” is full of fascinating history, sports legends, cultural landmarks, and quirky facts that make for some of the best trivia questions and answers.
Introduction
Chicago is more than just a big city on the shores of Lake Michigan—it is a hub of history, culture, music, architecture, and legendary sports teams. From the Great Chicago Fire of 1871 to the rise of deep-dish pizza, Chicago has left a lasting impression on the world. That’s why Chicago trivia questions and answers are so engaging: they test your knowledge of one of America’s most iconic cities.
In this article, we’ll explore Chicago through trivia, covering history, geography, culture, food, sports, and more. Each section provides interesting insights, making this both fun and educational. Whether you’re a teacher preparing quiz games, a trivia lover, or someone planning a Chicago-themed event, this article will guide you.
Chicago Trivia Questions and Answers
General Facts About Chicago
Q: In what year was Chicago officially incorporated as a city?
A: 1837
Q: What is Chicago’s nickname?
A: The Windy City
Q: Which U.S. state is Chicago located in?
A: Illinois
Q: What Great Lake borders Chicago?
A: Lake Michigan
Q: What is the population of Chicago (approximate 2020 census)?
A: About 2.7 million
Q: Where does Chicago rank in population among U.S. cities?
A: Third-largest city
Q: What is the tallest building in Chicago?
A: Willis Tower (formerly Sears Tower)
Q: What does the word “Chicago” mean in Native American language?
A: “Wild onion” or “wild garlic”
Q: What river famously flows backward due to engineering?
A: The Chicago River
Q: What colors are on the Chicago city flag?
A: White, blue, and red
History of Chicago
Q: Who is considered the founder of Chicago?
A: Jean Baptiste Point du Sable
Q: What year did the Great Chicago Fire occur?
A: 1871
Q: How many people were killed in the Great Chicago Fire?
A: About 300
Q: What major event helped rebuild Chicago and put it on the world stage in 1893?
A: The World’s Columbian Exposition
Q: Which gangster became infamous in Chicago during the 1920s?
A: Al Capone
Q: What was the site of violent labor unrest in 1886 in Chicago?
A: The Haymarket Riot
Q: In 1968, protests in Chicago took place during what major political event?
A: The Democratic National Convention
Q: Who was the first female mayor of Chicago?
A: Jane Byrne
Q: What was the nickname given to Chicago during the Prohibition era?
A: “The City of Gangs”
Q: What year did the Chicago Cubs finally win the World Series again after 108 years?
A: 2016
Chicago Architecture
Q: Chicago is known as the birthplace of what architectural style?
A: The skyscraper
Q: Who designed the Willis Tower?
A: Bruce Graham and Fazlur Rahman Khan
Q: What is the name of Chicago’s famous reflective sculpture in Millennium Park?
A: Cloud Gate (The Bean)
Q: What building was the tallest in the world from 1973 to 1998?
A: Sears Tower (now Willis Tower)
Q: Who is known as the “father of skyscrapers” in Chicago architecture?
A: Louis Sullivan
Q: What building is nicknamed the “corn cobs”?
A: Marina City Towers
Q: The John Hancock Center is now officially called what?
A: 875 North Michigan Avenue
Q: Which Chicago landmark is lit up with colors for holidays and events?
A: The Wrigley Building
Q: What is the name of the observatory in Willis Tower?
A: Skydeck Chicago
Q: What building was destroyed in the Great Fire and later rebuilt with a dome?
A: Chicago’s City Hall and Courthouse
Chicago Sports
Q: What MLB team plays at Wrigley Field?
A: The Chicago Cubs
Q: What is the name of Chicago’s other Major League Baseball team?
A: The Chicago White Sox
Q: What NBA team plays at the United Center?
A: The Chicago Bulls
Q: Who is the most famous player in Chicago Bulls history?
A: Michael Jordan
Q: What NFL team is based in Chicago?
A: The Chicago Bears
Q: Where do the Chicago Bears play their home games?
A: Soldier Field
Q: What NHL team plays in Chicago?
A: The Chicago Blackhawks
Q: How many Stanley Cups have the Blackhawks won?
A: Six
Q: What Chicago team won the 2005 World Series?
A: The Chicago White Sox
Q: Who threw the final out in the 2016 Cubs World Series victory?
A: Mike Montgomery
Chicago Food
Q: What style of pizza is Chicago famous for?
A: Deep-dish pizza
Q: Which local chain is famous for deep-dish pizza?
A: Giordano’s or Lou Malnati’s
Q: What is unique about a Chicago-style hot dog?
A: It is “dragged through the garden” with toppings, no ketchup
Q: What is the Italian beef sandwich known for in Chicago?
A: Thinly sliced beef dipped in au jus, served with peppers
Q: What is the name of the caramel-and-cheese popcorn mix Chicago made famous?
A: Garrett Mix (Chicago Mix)
Q: What Chicago-based company makes Cracker Jack?
A: Frito-Lay, but it originated in Chicago
Q: What sweet treat is Chicago the birthplace of?
A: The brownie
Q: Which famous fast-food chain originated in Chicago in 1940?
A: McDonald’s
Q: What is “Chicago mix” in popcorn terms?
A: A blend of caramel and cheese popcorn
Q: What is a Malört?
A: A bitter Chicago-made liquor
Chicago Music & Arts
Q: Chicago is considered the birthplace of what music genre?
A: Chicago blues
Q: What famous blues musician was based in Chicago?
A: Muddy Waters
Q: The band “Chicago” was originally called what?
A: Chicago Transit Authority
Q: What famous theater sign is a Chicago landmark?
A: The Chicago Theatre marquee
Q: What annual music festival is held in Grant Park?
A: Lollapalooza
Q: What is the name of the Chicago Symphony’s world-famous conductor who served from 1969 to 1991?
A: Sir Georg Solti
Q: What museum is home to Grant Wood’s American Gothic painting?
A: The Art Institute of Chicago
Q: Which comedian and actor founded Chicago’s Second City comedy troupe?
A: Paul Sills (with others, but he’s credited as founder)
Q: What is Chicago’s largest performing arts venue?
A: The Chicago Theatre
Q: Kanye West, a major rap artist, was born in what city?
A: Chicago
Chicago Politics
Q: Who was Chicago’s longest-serving mayor?
A: Richard J. Daley
Q: What was the nickname given to Chicago politics?
A: The Chicago Machine
Q: What future U.S. President worked as a community organizer in Chicago?
A: Barack Obama
Q: In what year was Harold Washington elected as Chicago’s first African American mayor?
A: 1983
Q: What political scandal in 1960 was linked to Chicago?
A: Allegations of voter fraud that helped John F. Kennedy win Illinois
Q: What is Chicago’s City Council often referred to as?
A: The “City Council Wars” (during political conflicts)
Q: Who became mayor of Chicago after Richard M. Daley retired?
A: Rahm Emanuel
Q: What famous Illinois governor linked to Chicago was impeached in 2009?
A: Rod Blagojevich
Q: Who is Chicago’s first openly gay mayor?
A: Lori Lightfoot
Q: What political convention held in Chicago in 1968 turned violent?
A: The Democratic National Convention
Chicago Landmarks
Q: What pier on Lake Michigan is one of Chicago’s top attractions?
A: Navy Pier
Q: What famous fountain is in Grant Park?
A: Buckingham Fountain
Q: What street is Chicago’s Magnificent Mile part of?
A: Michigan Avenue
Q: What planetarium is located in Chicago?
A: Adler Planetarium
Q: What famous aquarium is in Chicago?
A: Shedd Aquarium
Q: What natural history museum in Chicago is world-famous?
A: The Field Museum
Q: What giant sports arena is home to the Bulls and Blackhawks?
A: United Center
Q: What observatory offers glass-floor ledges over the city?
A: Skydeck Chicago (Willis Tower)
Q: What large public park hosts festivals like Taste of Chicago?
A: Grant Park
Q: What theater company is famous for sketch comedy?
A: Second City
Chicago Transportation
Q: What is the name of Chicago’s elevated train system?
A: The “L”
Q: How many lines does the Chicago “L” have?
A: Eight
Q: What is the busiest airport in Chicago?
A: O’Hare International Airport
Q: What is Chicago’s other major airport?
A: Midway Airport
Q: What train system connects Chicago to other cities across the Midwest?
A: Amtrak
Q: What is the longest street in Chicago?
A: Western Avenue
Q: What interstate highway runs directly through Chicago?
A: I-90 (Kennedy Expressway)
Q: What is Chicago’s Union Station used for?
A: Amtrak and commuter rail services
Q: The Chicago River is dyed green each year for what celebration?
A: St. Patrick’s Day
Q: What color is the CTA line that runs to O’Hare Airport?
A: Blue Line
Fun Facts & Pop Culture
Q: What popular sitcom was set in Chicago about a working-class family?
A: Married… with Children
Q: The 1986 movie Ferris Bueller’s Day Off was filmed in what city?
A: Chicago
Q: The 1990 Christmas movie Home Alone is set in which Chicago suburb?
A: Winnetka
Q: What superhero movie was filmed in Chicago to stand in for Gotham City?
A: The Dark Knight
Q: Oprah Winfrey’s famous talk show was based in what city?
A: Chicago
Q: The “Bean” sculpture in Millennium Park is officially called what?
A: Cloud Gate
Q: Chicago’s area code “312” is often used to symbolize what?
A: The heart of the city
Q: What TV medical drama is famously set in Chicago?
A: ER
Q: Chicago’s St. Valentine’s Day Massacre happened in what year?
A: 1929
Q: What famous talk show host got her start in Chicago?
A: Oprah Winfrey
Q: What professional wrestling event is frequently held in Chicago?
A: Allstate Arena WWE events (e.g., WrestleMania, Money in the Bank)
FAQs About Chicago Trivia Questions and Answers
1. Why is Chicago called the “Windy City”?
It’s partly due to its breezy weather, but also because of its reputation for political “wind” or boasting in the late 19th century.
2. What food is Chicago most famous for?
Deep-dish pizza and Chicago-style hot dogs are the most iconic.
3. What sports teams are based in Chicago?
The Cubs, White Sox, Bears, Bulls, and Blackhawks.
4. Is Chicago the biggest city in the U.S.?
No, it is the third-largest after New York City and Los Angeles.
5. What is Chicago’s most visited tourist attraction?
Millennium Park’s “Cloud Gate” (The Bean).
6. What is unique about the Chicago River?
It flows backward due to a historic engineering project.
7. When did Chicago host the World’s Fair?
1893 and 1933.
8. Which airport in Chicago is one of the busiest worldwide?
O’Hare International Airport.
9. What music is Chicago most known for?
Chicago blues and jazz.
10. Who is the most famous Chicago architect?
Frank Lloyd Wright contributed greatly, though his home base was Oak Park.
Conclusion
Chicago is a city with endless stories, traditions, and fun facts. From the Great Fire to deep-dish pizza and Michael Jordan’s legendary Bulls, Chicago trivia touches on every corner of history and culture. Playing trivia games about Chicago is not only fun but also educational, helping people appreciate this dynamic city.
Whether you’re planning a trivia night, teaching history, or simply love learning, these Chicago trivia questions and answers offer an exciting way to connect with the Windy City.
