109 Challenging Chicago Trivia & Facts

Are you a true Chicagoan at heart? Think you know everything about Chicago history? It’s time to put your knowledge to the test with our list of trivia questions and answers!

We’ve listed over 100 of the best Chicago questions for you to answer, or to challenge your friends and family with. These questions tackle everything there is to know about Chicago – from history and famous landmarks to iconic restaurants and famous Chicago celebrities. 

How does your knowledge of Chicago compare to that of other cities? Use our trivia questions to find out!

Chicago Trivia Questions and Answers

1. What year was Chicago founded?
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   1833.
2. What is Chicago’s official nickname?
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   The Windy City.
3. Which University has a campus in Hyde Park, Chicago?
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   The University of Chicago.
4. What is the name of Chicago’s tallest building?
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   Willis Tower (formerly known as Sears Tower).
5. What is Chicago’s official tree?
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   White Oak.
6. Which historic route begins or ends in Chicago?
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   Route 66.
7. What iconic landmark can be found at the intersection of Michigan Avenue and Congress Parkway?
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   Grant Park and Buckingham Fountain.
8. Which Chicago native is known as the “First Lady of American Cooking”?
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   Julia Child.
9. Which gangster reigned over Chicago during the Prohibition era?
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   Al Capone.
10. How many stars are on the Chicago flag?
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    Four.
11. What is Chicago’s oldest zoo?
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    Lincoln Park Zoo.
12. What famous street in Chicago is home to the Magnificent Mile?
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    Michigan Avenue.
13. Which Chicago neighborhood is known for its vibrant Mexican culture?
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    Pilsen.
14. What is the official flower of Chicago?
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    Chrysanthemum.
15. Which famous Chicago playwright is renowned for his play “Death of a Salesman”?
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    Arthur Miller.
16. Who is Chicago’s only World Heavyweight Boxing Champion?
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    Muhammad Ali.
17. Which Chicago landmark was originally built for the 1893 World’s Columbian Exposition, and is one of the largest science museums in the world?
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    The Museum of Science and Industry.
18. Major League Baseball’s first All-Star Game was played at Chicago’s Comiskey Park (named after former White Sox owner, Charles Comiskey) in what year?
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    1933.
19. What famous festival takes place annually in Grant Park?
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    Lollapalooza.
20. Which iconic Chicago sculpture is nicknamed “The Bean”?
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    Cloud Gate.
21. What is Chicago’s official animal?
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    White-tailed deer.
22. Which Chicago architect designed the iconic Home Insurance Building, considered the first modern skyscraper?
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    William Le Baron Jenney.
23. What is Chicago’s main airport?
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    O’Hare International Airport.
24. Which famous US President is buried in Chicago’s Oak Woods Cemetery?
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    Abraham Lincoln.
25. Who was the first African American mayor of Chicago?
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    Harold Washington.
26. How many neighborhoods does the Chicago area have?
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    178.
27. What are the names of Chicago’s Major League Baseball teams?
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    Chicago White Sox and Chicago Cubs.
28. Which famous lake lies east of Chicago?
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    Lake Michigan.
29. Who is considered the “father of modern improv” and co-founded The Second City, a renowned comedy theater in Chicago?
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    Del Close.
30. Which 1986 comedy film revolves around the story of two unemployed Chicago musicians who witness a murder?
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    The Blues Brothers.
31. What is the largest art museum in the United States, located in Chicago?
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    The Art Institute of Chicago.
32. What famous Chicago landmark lights up with different colors to celebrate special occasions?
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    The Chicago River.
33. Which NBA team is based in Chicago?
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    Chicago Bulls.
34. What planetarium in Chicago was also America’s first?
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    The Adler Planetarium.
35. Which famous comedian was born and raised in Chicago and starred in the TV series “The Office”?
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    Steve Carell.
36. Which Chicago neighborhood is known for its extensive collection of public art murals?
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    Wicker Park.
37. Which famous Chicago-born author wrote “Native Son” and “Black Boy”?
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    Richard Wright.
38. Which holiday parade attracts thousands of spectators on State Street every Thanksgiving?
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    The McDonald’s Thanksgiving Parade.
39. What famous Chicago skyscraper is known for its distinctive black framing?
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    John Hancock Center.
40. What landmark is situated at the end of the famous Route 66?
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    Lake Shore Drive.
41. What Chicago neighborhood is famous for its array of colorful Victorian-style houses?
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    Old Town.
42. Which Chicago newspaper won several Pulitzer Prizes for exposing corruption in the city?
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    Chicago Tribune.
43. What is the name of the Natural History Museum in Chicago?
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    The Field Museum.
44. Which iconic Chicago stadium was the home of the Chicago Bears from 1924 to 1970?
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    Wrigley Field.
45. Which popular music festival occurs annually in Chicago’s Union Park?
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    Pitchfork Music Festival.
46. What is the famous “El” in Chicago?
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    The city’s elevated train system.
47. What is the name of the Chicago-style hot dog chain that originated in Chicago and has locations across the United States?
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    Portillo’s.
48. Which famous blues singer is known as the “Empress of the Blues” and was born and raised in Chicago?
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    Bessie Smith.
49. What iconic Chicago landmark is shaped like a giant pair of eyeglasses?
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    The Chicago Riverwalk.
50. What is the name of the iconic sculpture in Grant Park that features a group of chrome-plated human figures?
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    Agora.
51. Which Chicago neighborhood is known for its vibrant LGBTQ+ community and annual Pride Parade?
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    Boystown.
52. Which Chicago street divides the city into east and west sections?
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    State Street.
53. Which Chicago location is home to the headquarters of McDonald’s Corporation?
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    Oak Brook.
54. What is the name of the annual outdoor music festival that features classical music performances?
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    Millennium Park Summer Music Series.
55. Which Chicago neighborhood is known for its thriving theater scene and is home to the Steppenwolf Theatre?
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    Lincoln Park.
56. Which legendary magician is strongly associated with Chicago, and even has a museum dedicated to him in the city?
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    Harry Houdini.
57. What is the name of the iconic Chicago restaurant that is a must-visit for its deep-dish pizza?
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    Giordano’s.
58. Which iconic Chicago neighborhood was the setting for the popular sitcom “Family Matters”?
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    Englewood.
59. What famous Chicago-born comedian is known for his role as George Costanza on the TV show “Seinfeld”?
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    Jason Alexander.
60. What is the name of the public park and beach located along Lake Michigan in the Hyde Park neighborhood?
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    Promontory Point.
61. Which famous Chicago-based radio station is known for its influential role in the development of house music?
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    WBMX.
62. What is the name of the Chicago Public Library’s flagship location that is known for its stunning architecture?
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    Harold Washington Library Center.
63. Which Chicago neighborhood is home to the iconic Music Box Theatre?
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    Lakeview.
64. What is the name of the iconic outdoor music venue located on Northerly Island?
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    Huntington Bank Pavilion.
65. Which NFL team calls Soldier Field their home stadium?
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    Chicago Bears.
66. Which Native American people were driven away from the Chicago area after 1830?
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    Navajo.
67. Which historic Chicago theater is the longest-running theater in the United States and is known for its opulent interior?
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    The Auditorium Theatre.
68. What is the name of the popular art festival held annually in Chicago’s Bucktown neighborhood?
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    Do Division Street Fest.
69. Which famous Chicago-born actor is known for his roles in movies such as “Ferris Bueller’s Day Off” and “The Producers”?
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    Matthew Broderick.
70. What is the name of the iconic Chicago jazz club that has hosted legendary musicians such as Charlie Parker and Miles Davis?
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    The Green Mill.
71. Which historic Chicago theater is known for its stunning marquee and is a popular venue for concerts and performances?
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    The Chicago Theatre.
72. What is the name of the iconic amusement park located on Chicago’s Navy Pier?
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    Centennial Wheel.
73. What is the name of the popular Chicago neighborhood known for its live music venues and historic architecture?
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    Uptown
74. Which famous Chicago-born chef is known for his innovative fusion cuisine and has multiple Michelin-starred restaurants in the city?
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    Grant Achatz.
75. What is the name of the famous Chicago blues club that has hosted iconic musicians such as Buddy Guy and Muddy Waters?
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    Kingston Mines.
76. Which Chicago suburb is home to the headquarters of McDonald’s Corporation?
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    Oak Brook.
77. What is the name of the famous fountain in Chicago’s Millennium Park that shoots water through its stainless steel plates?
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    Crown Fountain.
78. Which historic Chicago theater is known for its stunning marquee and is a popular venue for concerts and performances?
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    The Chicago Theatre.
79. What is the name of the popular street festival held annually in Chicago’s Wicker Park neighborhood?
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    Wicker Park Fest.
80. Which Chicago suburb is the birthplace of actress and comedian Tina Fey?
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    Evanston.
81. What is the name of the famous Chicago blues club that has hosted iconic musicians such as Buddy Guy and Muddy Waters?
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    Buddy Guy’s Legends.
82. Which Chicago neighborhood is home to the iconic Biograph Theater, where notorious gangster John Dillinger was ambushed and killed?
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    Lincoln Park.
83. What is the name of the historic Chicago theater that is known for its grand architecture and hosts a variety of performances?
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    The Oriental Theatre.
84. Which famous Chicago-born rapper is known for their contributions to the hip-hop genre and social activism?
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    Common.
85. What is the name of Jane Addam’s settlement house, located in the Near West Side?
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    Hull House.
86. What is the name of the famous landmark located in Chicago’s Millennium Park that resembles a stainless-steel bean?
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    Cloud Gate.
87. Chicago is the second most populous city in the U.S. True or False?
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    False! It is the third, after New York City and Los Angeles.
88. What is the name of the famous dance company based in Chicago that is known for its innovative choreography?
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    The Joffrey Ballet.
89. Which Chicago neighborhood is known for its vibrant art scene and is home to numerous art galleries and studios?
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    Ravenswood.
90. What is the name of the historic movie palace in Chicago that has been restored to its original splendor and hosts film screenings and live performances?
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    The Music Box Theatre.
91. Which Chicago suburb is the birthplace of actress and comedian Amy Poehler?
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    Burlington.
92. What is the name of the city’s large aquarium, which is also the third largest aquarium in the Western Hemisphere?
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    Shedd Aquarium.
93. Which famous Chicago-born comedian is known for his unique style of improvisational comedy and starred in the TV show “Whose Line Is It Anyway?”?
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    Wayne Brady.
94. What is the name of the outdoor street fair held annually in Chicago’s Andersonville neighborhood that features live music, local vendors, and food?
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    Midsommarfest.
95. What year was the Great Chicago Fire?
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    1871.
96. Which basketball player led the Chicago Bulls to win six NBA championships?
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    Michael Jordan.
97. Chicago is the fifth largest city in the U.S. True or False?
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    False! It is the third largest city.
98. What was first broadcast from Chicago’s CBS Studios on September 26, 1960?
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    The first televised U.S. Presidental Candidates’ Debate.
99. What was originally in place of the Navy Pier Centennial Wheel?
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    Navy Pier’s first, Ferris Wheel, which was inspired by the 1893 Ferris Wheel at the World’s Columbian Exposition.
100. Which race was first held in Downtown Chicago in 1895?
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     The Chicago Times-Herald Automobile Race..
101. When was the Sears Tower (now the Willis Tower) built?
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     1973.
102. Which iconic Chicago buildings survived the Great Chicago Fire?
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     The Chicago Water Tower and Pumping Station.
103. Which legendary African-American woman famously made Chicago her home for most of her career?
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     Oprah Winfrey.
104. Which museum in Chicago is home to the largest dinosaur ever discovered?
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     The Field Museum.
105. The University of Chicago campus is home to a large bronze sculpture designed by which artist?
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     Henry Moore.
106. Chicago has many nicknames – can you list them?
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     The Windy City, The White City, The City of Big Shoulders, The City That Works, and The Second City.
107. Wrigley Field is now home to which of Chicago’s sports teams?
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     Chicago Cubs.
108. Which zoo was the first in the world to successfully perform brain surgery on a gorilla?
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     Chicago’s Brookfield Zoo.
109. Former First Lady Michelle Obama was the director of the Chicago Branch of which social justice organization?
     Show answer
     Public Allies.

From Downtown Chicago to Lake Michigan, See How Much You Know About This Famous City!

Once you’ve answered these questions, you can test your friends and family to see who knows the most about this iconic city. Our questions and answers are a great entry into learning more about the fascinating history, culture, and landmarks of Chicago. Happy quizzing!

Eleanor Griffiths

Eleanor is a qualified English teacher and has received a Post Graduate Diploma in Education (PGDE), specializing in Secondary English, and holds a BA (Hons) in English Literature from Liverpool John Moores University. She is certified to teach English as a foreign language (TEFL) and has worked with students in the U.K. and South East Asia. She currently works as an English teacher in Vietnam, teaching students across a range of ages.

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