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Quizzes > Geography

Chicago trivia questions: Test your Windy City smarts

Quick, free Chicago quiz to test your knowledge. Instant results.

Editorial: Review CompletedCreated By: Nicholas BittencourtUpdated Aug 24, 2025
Difficulty: Moderate
2-5mins
Learning OutcomesCheat Sheet
Paper art illustration for Chicago trivia quiz featuring landmarks, deep-dish pizza, sports legends on golden yellow background

This quiz lets you tackle Chicago trivia questions and see how much you know about landmarks, deep-dish, neighborhoods, history, and hometown sports. If football is your thing, try Chicago Bears trivia to test your football knowledge, or go broader with an Illinois quiz that spans the whole state.

Which river is famously dyed green each St. Patrick's Day in Chicago?
Chicago River
Lake Michigan
Calumet River
Chicago Waterway
Each year on St. Patrick's Day, the Chicago River is dyed a bright green as part of the city's celebration of Irish heritage. This tradition began in 1962 when city plumbers used green dye to trace illegal sewage discharges and noticed the festive potential. The environmentally safe, vegetable-based dye transforms the river for a day and draws massive crowds along the riverbanks.
What is the name of Chicago's lakefront park that houses Buckingham Fountain?
Jackson Park
Lincoln Park
Millennium Park
Grant Park
Buckingham Fountain, one of the largest fountains in the world, is located in Grant Park, often called 'Chicago's front yard.' Dedicated in 1927, the fountain is a major landmark and operates on a rigorous schedule of water shows from spring through fall. Grant Park spans 319 acres along Lake Michigan and includes other attractions such as the Art Institute of Chicago.
Which Chicago skyscraper, formerly known as Sears Tower, was once the tallest building in the world?
Aon Center
Willis Tower
John Hancock Center
Trump International Hotel and Tower
Originally completed in 1973 as the Sears Tower, this skyscraper held the title of the world's tallest building for 25 years. In 2009, it was renamed Willis Tower after a London-based insurance broker acquired naming rights. Standing at 1,450 feet, its distinctive black aluminum and bronze-tinted glass façade remains an iconic feature of Chicago's skyline.
Chicago is famously known for which style of pizza featuring a deep crust and generous toppings?
Sicilian pizza
Deep-dish pizza
Neapolitan pizza
New York-style pizza
Deep-dish pizza, which originated in Chicago in the 1940s, is characterized by its high-edged crust that allows for layers of cheese, toppings, and chunky tomato sauce. Unlike traditional thin-crust pizzas, it's baked in a round, steel pan leading to a thick, pie-like structure. This style has become one of Chicago's most celebrated culinary exports.
What color are the most common taxi cabs in Chicago?
Blue
Red
Yellow
Green
Yellow taxi cabs are the most commonly seen licensed taxicabs in Chicago, following a standardized color scheme adopted years ago. Their bright hue enhances visibility in the city's busy streets. While ride-share services have grown, yellow cabs remain an iconic element of Chicago transportation.
Which Chicago team won the 2016 World Series, ending a 108-year championship drought?
Chicago Bears
Chicago Bulls
Chicago Cubs
Chicago White Sox
The Chicago Cubs clinched the 2016 World Series by defeating the Cleveland Indians in a thrilling Game 7 that ended in extra innings. This victory broke the Cubs' 108-year drought, the longest in major North American sports history. The win sparked massive celebrations throughout Chicago and among fans worldwide.
What is the name of Chicago's landmark museum located on Michigan Avenue featuring a notable collection of Impressionist art?
Field Museum
Art Institute of Chicago
Museum of Science and Industry
Shedd Aquarium
The Art Institute of Chicago, established in 1879, is renowned for its extensive collection of Impressionist and Post-Impressionist paintings, including works by Monet and Renoir. Situated on Michigan Avenue's Museum Campus, it also boasts an expansive range of modern and contemporary art. Its classical Beaux-Arts building and modern wing draw millions of visitors yearly.
Chicago's 'El' system refers to what mode of public transportation?
Bus network
Ferry service
Elevated train system
Subway system
The Chicago 'El' (short for elevated) is the city's rapid transit system, known for its elevated steel tracks that snake through downtown and outlying neighborhoods. Operated by the Chicago Transit Authority (CTA), it opened in 1892, making it one of the oldest urban rail systems in the U.S. The system's iconic loop around the downtown area gives it its name, the 'Loop'.
Which Chicago NBA franchise won six championships during the 1990s?
Chicago Sky
Chicago Packers
Chicago Stags
Chicago Bulls
The Chicago Bulls, led by Michael Jordan, won six NBA championships between 1991 and 1998, securing two separate three-peats. Their dominance under coach Phil Jackson established one of the league's greatest dynasties. The team's success solidified Chicago's reputation as a basketball city.
Chicago's alternative nickname includes the phrase 'City of the ____'?
Big Shoulders
Skyscrapers
Broad Water
Wind
Chicago is often called the 'City of the Big Shoulders,' a phrase coined by poet Carl Sandburg in his 1914 Chicago Poems, referring to the city's industrial strength and robust spirit. The nickname captures Chicago's role as a major manufacturing and transportation hub in the early 20th century. It remains a celebrated descriptor of the city's character.
Which annual festival in Chicago is famed for showcasing the city's best local food vendors in Grant Park?
Taste of Chicago
Chicago Food Expo
Chicago Gourmet
Windy City Smokeout
Taste of Chicago, established in 1980, is the world's largest food festival, featuring dishes from Chicago's top restaurants and local vendors in Grant Park. Held over five days every summer, it offers music, cooking demonstrations, and family activities. It draws millions of visitors eager to sample the city's culinary diversity.
Which Chicago-born author is famous for writing 'Native Son' and 'Black Boy'?
Gwendolyn Brooks
Ernest Hemingway
Richard Wright
Saul Bellow
Richard Wright, associated with Chicago's South Side, authored the influential novels 'Native Son' (1940) and 'Black Boy' (1945). His works explore racial themes and the African American experience in early 20th-century America. Wright's writing had a profound impact on American literature and civil rights discourse.
Which Chicago neighborhood is renowned for its Mexican-American culture and vibrant murals?
Lincoln Park
Pilsen
Hyde Park
Wicker Park
Pilsen, located on Chicago's Lower West Side, has been a hub for Mexican-American culture since the mid-20th century. It is celebrated for its colorful street murals, authentic Mexican restaurants, and the National Museum of Mexican Art. The neighborhood's cultural events and galleries attract both residents and tourists.
What large annual free event features aerobatic performances and boat demonstrations along Chicago's lakefront each August?
Navy Pier Fireworks
Taste of Chicago
Chicago Air and Water Show
Lollapalooza
The Chicago Air and Water Show, dating back to 1959, showcases high-speed aerial acrobatics by military and civilian pilots as well as water-based demonstrations by skilled boat teams. Held over two days in August, it is one of the city's largest free public events, drawing over two million spectators. The show runs along the Lake Michigan shoreline, providing expansive viewing areas.
Which original NFL franchise was based in Chicago before relocating and eventually becoming the Arizona Cardinals?
Chicago Cardinals
Chicago Bears
Chicago Hawks
Chicago Wolves
The Chicago Cardinals were a founding member of the NFL in 1920. After several relocations to St. Louis and then Phoenix, they became the Arizona Cardinals. This team shares the distinction of being one of the oldest continuously run professional football franchises in the United States.
In which park is the iconic Cloud Gate sculpture, known as 'The Bean,' located?
Millennium Park
Jackson Park
Lincoln Park
Grant Park
Cloud Gate, nicknamed 'The Bean,' is a famous reflective sculpture by artist Anish Kapoor installed in 2006 at Millennium Park. Its seamless, mirror-like surface reflects Chicago's skyline and the surrounding park, making it one of the city's most photographed landmarks. Millennium Park, part of Chicago's larger Grant Park area, hosts numerous cultural events year-round.
Which Chicago landmark residence, designed by Frank Lloyd Wright, is a quintessential example of Prairie School architecture?
Taliesin West
Robie House
Fallingwater
Guggenheim Museum
The Frederick C. Robie House in Hyde Park, completed in 1910, is one of Frank Lloyd Wright's best-known Prairie School designs. Its horizontal lines, overhanging eaves, and integration with the landscape exemplify Wright's vision. The house is a National Historic Landmark and is open to the public for tours.
In which year did the infamous St. Valentine's Day Massacre occur in Chicago?
1931
1925
1929
1922
On February 14, 1929, seven members and associates of Chicago's North Side Gang were murdered in what became known as the St. Valentine's Day Massacre. The event is widely attributed to Al Capone's gang and marked a significant moment in organized crime history. The massacre underscored the violence of Prohibition-era America.
Which museum in Chicago is home to Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered?
Chicago History Museum
Museum of Science and Industry
Field Museum
Shedd Aquarium
Sue, named after its discoverer Sue Hendrickson, is a 42-foot-long T. rex skeleton housed at Chicago's Field Museum since 2000. It is the largest, most complete, and best-preserved T. rex specimen known, providing invaluable insights into dinosaur anatomy and behavior. The exhibit attracts paleontology enthusiasts from around the world.
Which public art sculpture in Chicago features a 50-foot-tall red steel structure designed by Alexander Calder?
Cloud Gate
Flamingo
Chicago Picasso
Crown Fountain
Flamingo, unveiled in 1974, is a monumental red steel sculpture by Alexander Calder located in the Federal Plaza of downtown Chicago. Its vivid color and abstract form contrast with surrounding architecture, creating a striking urban landmark. Calder's signature style and scale have made Flamingo an enduring piece of public art.
Which Chicago blues musician, dubbed the 'Father of Chicago Blues,' greatly influenced modern electric blues?
Muddy Waters
Howlin' Wolf
Buddy Guy
B.B. King
Muddy Waters moved from Mississippi to Chicago in the 1940s, electrifying Delta blues and pioneering the Chicago blues style. His use of electric guitar and band arrangements influenced rock and blues musicians worldwide. Waters's recordings at Chess Records became foundational to modern blues music.
Who designed the Modern Wing of the Art Institute of Chicago, which opened in 2009?
Frank Gehry
I.M. Pei
Renzo Piano
Zaha Hadid
Renzo Piano, a Pritzker Prize-winning architect, designed the Modern Wing of the Art Institute of Chicago, completed in May 2009. The addition nearly doubled the museum's gallery space and introduced contemporary design elements. Piano's use of glass and steel emphasizes light and openness in the new wing.
The University of Chicago's athletic teams are nicknamed what?
Wildcats
Hawks
Blue Demons
Maroons
The University of Chicago Maroons compete in NCAA Division III athletics and have a rich sports history. The name 'Maroons' is derived from the school's official color. The university was a founding member of the Big Ten Conference before focusing on academics and smaller-scale athletics.
Which landmark skyscraper, completed in 1925, features two towers connected by skybridges and once served as home to the Chicago Tribune?
Willis Tower
Tribune Tower
Sears Tower
Wrigley Building
Tribune Tower, completed in 1925, is a neo-Gothic skyscraper on North Michigan Avenue that housed the Chicago Tribune newspaper. Its twin setbacks and flying buttresses set it apart as an architectural landmark. Stones from famous global sites were embedded in its lower walls after an architectural competition that spanned several countries.
In what year was the Home Insurance Building in Chicago, often considered the world's first skyscraper, completed?
1890
1901
1885
1871
The Home Insurance Building, completed in 1885, is widely regarded as the world's first skyscraper due to its pioneering use of a steel-frame structure. Located in Chicago's Loop, it stood 10 stories tall and laid the groundwork for modern high-rise construction. Although demolished in 1931, its legacy endures in skyscraper design.
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Study Outcomes

  1. Recognize Iconic Chicago Landmarks -

    Recall the names, history, and significance of famous sites like Willis Tower, Cloud Gate, and Navy Pier.

  2. Recall Deep-Dish Pizza Facts -

    Discover key trivia about the origins, ingredients, and regional variations of Chicago's signature deep-dish pizza.

  3. Analyze Sports Legends' Achievements -

    Identify notable milestones and contributions of Chicago's legendary athletes across baseball, basketball, and football.

  4. Test Personal Knowledge of Chicago Trivia -

    Answer scored questions to gauge your expertise on Chicago facts and receive instant feedback.

  5. Compare Scores with Friends -

    Challenge friends to the quiz, measure who has the highest Chicago IQ, and enjoy friendly competition.

  6. Explore Fun Chicago Facts -

    Uncover surprising tidbits about the Windy City's culture, history, and hidden gems beyond the quiz questions.

Cheat Sheet

  1. Skyline Showstoppers -

    Chicago's skyline is crowned by the Willis Tower (formerly Sears Tower) at 1,450 ft, making it one of the tallest in the Western Hemisphere (Chicago Architecture Center). Use the mnemonic "Willis Wins" to recall it outranked the Hancock. Knowing this helps you ace chicago trivia questions on skyscraper heights.

  2. Deep-Dish Origins -

    Pizzeria Uno served the first deep-dish pizza in 1943, created by Ike Sewell and Rudy Malnati Sr., as documented by the University of Illinois Rare Book Library. Remember "UNO starts the funo" to link the year '43 with Uno's debut. This tidbit is a staple in chicago trivia questions and answers about local cuisine.

  3. Sports Legends -

    Michael Jordan led the Chicago Bulls to six NBA titles in the 1990s, while Walter Payton ("Sweetness") rushed for over 16,000 yards with the Chicago Bears (Pro Football Hall of Fame). A simple trick: Bulls 6 + Bears 16 = two iconic numbers to remember. Perfect for any Chicago trivia quiz question on athletic greats.

  4. Great Chicago Fire Facts -

    The Great Chicago Fire of 1871 consumed more than 3 sq miles and destroyed over 17,000 structures (Chicago History Museum). Recall "O'Leary's cow" as the legendary - though unproven - spark. This story often pops up in Chicago facts quiz segments about city history.

  5. Public Art & Landmarks -

    Millennium Park's Cloud Gate ("The Bean") was unveiled in 2006 and reflects 168,000 lbs of polished stainless steel (Chicago Department of Cultural Affairs). Think "Bean equals sheen" to picture its mirror finish. This is a go-to fact for anyone looking to test your Chicago knowledge on modern art installations.

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