Chicago
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125 free Chicago trivia questions with answers — geography quiz, new questions added Aug 2026.
17 free Chicago trivia questions with answers. Think you know everything about Chicago? Put your knowledge to the test with our engaging 125-question trivia quiz covering the city's rich history, iconic landmarks, cultural significance, and famous residents. Whether you're a Chicago native or a curious visitor, this quiz will challenge what you know about the Windy City.
30 of 125 questions with answers and explanations. Play the quiz
Q 01Which restaurant is often credited with inventing Chicago-style deep-dish pizza?
Pizzeria Uno
Pizzeria Uno, founded by Ike Sewell and Ric Riccardo in 1943, is widely credited as the birthplace of Chicago-style deep-dish pizza.
Q 02In what year did the Great Chicago Fire occur?
1871
The Great Chicago Fire began on October 8, 1871, in a barn on DeKoven Street and burned for two days; the cow-kicking-a-lantern story was later admitted to be a reporter's invention.
Q 03Which Major League Baseball team plays its home games at Wrigley Field?
Chicago Cubs
Wrigley Field, famous for its ivy-covered outfield walls, has been the iconic home stadium for the Chicago Cubs baseball team since 1916.
Q 04What is the official name of the 'Bean' sculpture in Millennium Park?
Cloud Gate
Cloud Gate is Anish Kapoor's official title for the sculpture; its 168 welded stainless-steel plates were polished so no seams show, and Kapoor initially disliked the Bean nickname.
Q 05Which Chicago institution is home to Sue, one of the most complete T. rex skeletons?
Field Museum
The Field Museum has displayed Sue, a roughly 90-percent-complete Tyrannosaurus rex unearthed in South Dakota in 1990, since 2000.
Q 06Under what name did the 110-storey Loop skyscraper now called Willis open in 1973?
Sears Tower
Completed in 1973, the Willis Tower was originally known as the Sears Tower and held the title of the world's tallest building for nearly 25 years.
Q 07Which director of teen comedies like 'Ferris Bueller's Day Off' often set his films in Chicago and its suburbs?
John Hughes
Filmmaker John Hughes frequently used Chicago and its surrounding suburbs as the backdrop for his iconic 1980s teen films, including 'Ferris Bueller's Day Off.'
Q 08How many NBA championships did the Chicago Bulls win with Michael Jordan in the 1990s, all of them between 1991 and 1998?
6
6 titles came as two three-peats, 1991-93 and 1996-98, split by Jordan's brief retirement to play minor-league baseball.
Q 09Chicago is the hub of an electrified, urban form of which genre, carried north by the Great Migration?
Blues
Blues is the genre: Chicago blues, the amplified urban form, was defined by Muddy Waters, Howlin' Wolf and Willie Dixon at Chess Records after the Great Migration brought Delta musicians north.
Q 10Which trader of African descent is recognised as the first permanent non-indigenous settler of what became Chicago?
Jean Baptiste Point du Sable
Jean Baptiste Point du Sable, a trader of African descent from Haiti, built the first permanent settlement at Chicago in the late 18th century.
Q 11Which famous American highway, nicknamed 'The Mother Road' in Steinbeck's The Grapes of Wrath, historically begins in Chicago?
Route 66
Route 66 was established in 1926 and runs from Chicago all the way to Los Angeles; Steinbeck's 1939 novel popularised the Mother Road nickname.
Q 12The city's Mercantile Exchange started life in 1898 under what agricultural name?
Butter and Egg Board
The Chicago Mercantile Exchange (CME) was originally founded in 1898 as the Chicago Butter and Egg Board, trading agricultural commodities.
Q 13Which NFL team moved its home games to Soldier Field in 1971?
Chicago Bears
Q 21A donation from which country after the Great Chicago Fire spurred the founding of Chicago Public Library?
The United Kingdom
The United Kingdom: after the 1871 fire Thomas Hughes organised a British donation of some 8,000 books, and Chicago Public Library opened in 1873 inside a former iron water tank.
Q 22A statue of which Roman goddess crowns the Chicago Board of Trade Building?
Ceres
Ceres, Roman goddess of grain, tops the 1930 Art Deco tower as a 31-foot faceless aluminum statue by John Storrs, fitting an exchange built on wheat and corn futures.
Q 23Which engineer of Skidmore, Owings & Merrill worked with architect Bruce Graham on the Willis Tower?
Fazlur Rahman Khan
The Chicago Bears made Soldier Field their full-time home in 1971 after fifty seasons at Wrigley Field; they had played occasional games there as early as 1926.
Q 14What is the approximate average elevation of Chicago above sea level?
580 feet (177 meters)
Chicago sits on a relatively flat plain, with an average elevation of approximately 579 feet (176 meters) above sea level, though some areas like Blue Island reach higher points.
Q 15In 2025 Chicago Fire FC announced a privately funded soccer stadium as the anchor of which riverside development just south of Roosevelt Road?
The 78
The 78 is Related Midwest's 62-acre riverside site; in June 2025 owner Joe Mansueto unveiled a privately funded 22,000-seat stadium there, ending the club's moves between Soldier Field and suburban Bridgeview.
Q 16On what date was the City of Chicago incorporated?
March 4, 1837
March 4, 1837 was a Saturday, and for several decades afterwards Chicago was the fastest-growing city in the world.
Q 17According to the 2020 census, roughly what was Chicago's population?
2.7 million
The 2020 census counted 2,746,388 Chicagoans, roughly 2.7 million, a slight rise from 2,695,598 in 2010.
Q 18Which indigenous people inhabited the Chicago area in the mid-18th century?
Potawatomi
The Potawatomi held the Chicago area by the mid-18th century, having succeeded the Miami, Sauk and Meskwaki peoples; they ceded the land in the 1833 Treaty of Chicago.
Q 19The Great Chicago Fire of October 1871 killed roughly how many people?
About 300
About 300 people are thought to have died; the fire destroyed some 17,000 structures across 3.3 square miles and left more than 100,000 homeless.
Q 20In 1997, the Chicago City Council formally exonerated whom of blame for the Great Chicago Fire?
Catherine O'Leary
Catherine O'Leary and her cow were cleared by a 1997 City Council resolution; reporter Michael Ahern admitted in 1893 that he had invented the lantern-kicking story.
More than 1.7 million people a year visit its Skydeck, the highest observation deck in the US.
Q 24The Sanitary and Ship Canal permanently reversed the Chicago River's flow in which year?
1900
1900: the Chicago Sanitary and Ship Canal opened that January, sending the city's sewage toward the Mississippi watershed instead of its Lake Michigan drinking water.
Q 25Chicago's Y-shaped civic symbol, seen on buildings across the city, represents what?
The three branches of the river
The three branches of the river: the Municipal Device's Y stands for the North and South Branches meeting the main stem at Wolf Point; it came out of an 1892 Chicago Tribune contest.
Q 26Which talk-show host taped her syndicated daytime show in Chicago from 1986 to 2011?
Oprah Winfrey
Oprah Winfrey took her show national from Chicago in September 1986 and ended its 25-season run there in May 2011; her production company built its West Loop studios in 1990.
Q 27Which substance inspired the mirror-like form of Millennium Park's sculpture nicknamed 'The Bean'?
Liquid mercury
Liquid mercury was Kapoor's inspiration; the surface reflects and distorts the skyline and the clouds overhead, and the whole thing weighs 110 short tons.
Q 28Wrigley Field opened in 1914 under what name?
Weeghman Park
Weeghman Park, named for Whales owner Charles Weeghman, was built for the Federal League's Chicago Whales in 1914; it is the second-oldest major-league park after Fenway.
Q 29In what year did Wrigley Field become the last MLB park to install lights for night games?
1988
1988: Wrigley Field's first scheduled night game, on August 8, 1988, was rained out and the first complete one played the next night, making it the last MLB park to add lights.
Q 30The 1893 Chicago world's fair marked the 400th anniversary of what?
Columbus's landing in the Americas
Columbus's landing in the Americas was in 1492, yet the World's Columbian Exposition ran from May 1 to October 30, 1893, and drew more than 27 million visitors.