Chicago
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121 free Chicago trivia questions with answers — geography quiz, new questions added Oct 2026.
17 free Chicago trivia questions with answers. Think you know everything about Chicago? Put your knowledge to the test with our engaging 121-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 121 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's co-founder Ike Sewell first wanted to open a Mexican restaurant; some credit the deep-dish recipe itself to an early employee, Rudy Malnati, whose son Lou later started a rival chain.
Q 02Legend blames which animal for starting the Great Chicago Fire?
Cow
Cow: the tale of a kicked-over lantern was in print soon after the fire, though a reporter later admitted that the story had been made up.
Q 03Which president-elect gave his election-night victory speech to a huge crowd in Chicago's Grant Park?
Barack Obama
Barack Obama held his 2008 rally in his adopted home city, in the same park where police and protesters had clashed during the 1968 Democratic convention.
Q 04What is the official name of the 'Bean' sculpture in Millennium Park?
Cloud Gate
Cloud Gate is Anish Kapoor's own title for the piece; the public coined 'the Bean' while it was being built, and Kapoor at first dismissed the nickname.
Q 05Which Chicago institution is home to Sue, one of the most complete T. rex skeletons?
Field Museum
The Field Museum won Sue at a 1997 auction, with McDonald's and Disney helping to pay, after a five-year fight over who owned the South Dakota fossil.
Q 06Under what name did the 110-storey Loop skyscraper now called Willis open in 1973?
Sears Tower
Sears Tower was the name until 2009, when London insurance broker Willis Group leased offices there and got the naming rights; Sears itself had moved out in the 1990s.
Q 07Which director set 1980s teen comedies such as 'Ferris Bueller's Day Off' in Chicago and its North Shore suburbs?
John Hughes
John Hughes grew up in suburban Northbrook, once called Shermerville, and set several of his films in a fictional Shermer, Illinois, modelled partly on it.
Q 08Between the Bulls' two 1990s title three-peats, Michael Jordan retired from basketball to play which sport professionally?
Baseball
Baseball: Jordan quit the NBA in October 1993 and spent 1994 with the minor-league Birmingham Barons, batting .202, before returning to win three more titles.
Q 09Chicago is the hub of an electrified, urban form of which genre, carried north by the Great Migration?
Blues
Blues: Delta players who came north swapped acoustic guitars for electric ones so they could be heard in Chicago's noisy clubs, and Muddy Waters bought his first in 1944.
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 ran a trading farm at the mouth of the Chicago River until 1800; in 2021 the city renamed the outer part of Lake Shore Drive in his honour.
Q 11Which famous American highway, nicknamed 'The Mother Road' in Steinbeck's The Grapes of Wrath, historically begins in Chicago?
Route 66
Route 66 ran from Chicago to Santa Monica, California; as interstates replaced it stretch by stretch, it was dropped from the US highway system in 1985.
Q 12Which Chicago exchange, later famous for pork belly futures, began in 1898 trading butter and eggs?
Chicago Mercantile Exchange
The Chicago Mercantile Exchange started as the Chicago Butter and Egg Board, took its present name in 1919, and in 1972 opened the first futures market in foreign currencies.
Q 13Which team left Wrigley Field after decades there to make Soldier Field its home in 1971?
Q 21A donation from which country after the Great Chicago Fire spurred the founding of Chicago Public Library?
The United Kingdom
The United Kingdom: a British book drive backed by the author of Tom Brown's School Days sent some 8,000 volumes, and the library opened in 1873 inside an old circular 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 faceless aluminum statue by John Storrs, a nod to 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
Chicago Bears
The Chicago Bears had to go: after the AFL-NFL merger the league wanted stadiums seating at least 50,000, and Wrigley Field held too few.
Q 14In the 1850s and 1860s Chicago jacked up its downtown streets and buildings by several feet to make room for what?
A sewer system
A sewer system: the city sat too low to drain, so engineers laid the pipes on top of the old streets, covered them over, and lifted whole brick buildings on jackscrews to the new level.
Q 15In 2025 Chicago Fire FC announced a privately funded soccer stadium as the anchor of which riverside development?
The 78
The 78 is named as a would-be 78th neighbourhood beside Chicago's 77 official community areas; the club broke ground on the stadium there in March 2026.
Q 16Chicago's name is usually traced to an Algonquian word for which pungent plant that once grew thickly there?
Wild onion
Wild onion: the name was the river's first, noted by travellers in the 1600s, and the town that later grew up at its mouth took it from the river.
Q 17At the 2020 census, which city besides New York was more populous than Chicago?
Los Angeles
Los Angeles passed Chicago in population in the 1980s; until then only New York had outranked the Midwestern city since 1890.
Q 18Which indigenous people inhabited the Chicago area in the mid-18th century?
Potawatomi
The Potawatomi gave up the last of their land around Chicago in an 1833 treaty signed there, in return for payments and tracts west of the Mississippi.
Q 19The Great Chicago Fire of October 1871 killed roughly how many people?
About 300
About 300 people died, though some 17,000 buildings burned and 100,000 residents lost their homes; Fire Prevention Week is held each October to mark the anniversary.
Q 20In 1997, the Chicago City Council formally exonerated whom of blame for the Great Chicago Fire?
Catherine O'Leary
Catherine O'Leary was cleared after amateur historian Richard Bales argued the fire more likely began with a neighbour, Daniel 'Peg Leg' Sullivan, the man who first raised the alarm.
Fazlur Rahman Khan's 'bundled tube' design ties nine square tubes together so they brace one another against the wind, which let the tower climb to 110 storeys.
Q 24Chicago reversed its river's flow in 1900 chiefly to protect what?
Drinking water
Drinking water came from Lake Michigan, where the river had been carrying the city's waste and raising fears of disease; since 1900 a canal has drawn the flow away from the lake, toward the Mississippi.
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 came to Chicago in 1984 to host the low-rated AM Chicago; within months it had overtaken Donahue in the local ratings, and in 1986 it went national under her name.
Q 27Which substance inspired the mirror-like form of Millennium Park's sculpture nicknamed 'The Bean'?
Liquid mercury
Liquid mercury inspired the seamless skin: the sculpture was unveiled unfinished in 2004 with its weld lines showing, then tented while crews ground and polished them away.
Q 28Which climbing plant has covered the brick outfield walls of Wrigley Field since 1937?
Ivy
Ivy was planted along the walls in 1937 at the urging of Bill Veeck; under the park's ground rules, a ball that gets stuck in the vines is a ground-rule double.
Q 29In 1988 Wrigley Field became the last major-league ballpark to add what?
Lights for night games
Lights for night games arrived on 8 August 1988, and rain washed out that first night; lights bought for 1942 had been given to the war effort after Pearl Harbor.
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 came in 1492: the fair was dedicated in October 1892, but its gates opened to the public only the following May.