92 Chicago Trivia Questions and Answers

Welcome to the ultimate Chicago Trivia post! From its rich history to its vibrant cultural scene, Chicago has countless fascinating facets. Whether you’re a lifelong resident or you’ve never visited the Windy City, there’s something new to learn for everyone. Below, you’ll find a series of questions and answers that explore everything from Chicago’s famous landmarks, sports venues, and notable residents to its significant events, unique culinary treats, and influential contributions to the arts. So, are you ready to test your knowledge and delve into the captivating world of Chicago? Let’s go!

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1. What is the nickname of Chicago?

2. Which famous American architect designed numerous buildings in Chicago?

3. What body of water lies along the eastern side of Chicago?

4. Which iconic American road starts in Chicago?

5. What Chicago park houses a zoo and a conservatory?

6. What is the tallest building in Chicago?

7. What Chicago location was designated a National Historic Landmark in 2006?

8. What famous Chicago gangster was also known as ‘Scarface’?

9. Which popular food style is Chicago known for?

10. Which university in Chicago was established by John D. Rockefeller?

11. Who was the mayor of Chicago from 1989 to 2011?

12. What large museum in Chicago was founded in 1893?

13. What river flows through the city of Chicago?

14. What annual event dyes the Chicago River green?

15. In what year was the Chicago Fire?

16. What famous American talk show host is based in Chicago?

17. What’s the name of the 110-story skyscraper in Chicago that was once the tallest building in the world?

18. What is the name of the world-class symphony orchestra based in Chicago?

19. What is the name of the famous fountain located in Grant Park?

20. What is the name of Chicago’s main airport?

21. What is the professional NBA team of Chicago?

22. What is the professional baseball team of Chicago?

23. What is the professional NFL team of Chicago?

24. What is the name of the science museum in Chicago with a full size replica of a coal mine?

25. What is the name of Chicago’s premier art museum?

26. What famous Chicago sandwich has slices of roast beef served on an Italian roll and often dipped in gravy?

27. What neighborhood in Chicago is known for its vibrant nightlife and entertainment?

28. What is the largest park in Chicago?

29. What large lagoon in Chicago’s Lincoln Park is popular for birdwatching?

30. What annual music festival takes place in Chicago’s Grant Park?

31. Who was Chicago’s first African-American mayor?

32. Which Chicago university is well-known for its business school?

33. In which Chicago neighborhood is the former home of President Barack Obama?

34. What Chicago avenue is known for its high-end shops and boutiques?

35. Which Chicago neighborhood is known for its large LGBT community?

36. Which president was elected while living in Chicago?

37. What is the famous reflective sculpture located in Chicago’s Millennium Park?

38. Who designed the Cloud Gate sculpture?

39. What is the name of Chicago’s free zoo?

40. What is the name of the theme park located just outside of Chicago?

41. What is the main ingredient in a Chicago-style hot dog?

42. What large aquarium is located in Chicago?

43. What is the tallest building in the Western Hemisphere, located in Chicago?

44. What Chicago-based film critic co-hosted a long-running movie review TV show?

45. What classic movie featuring Jake and Elwood Blues is set in Chicago?

46. What annual marathon takes place in the streets of Chicago?

47. What famous dish made with cheese, caramel, and butter popcorn originated in Chicago?

48. What is the name of the largest art museum in Chicago?

49. What was the name of the World’s Fair held in Chicago in 1893?

50. What Chicago publication is one of the largest newspapers in the United States?

51. Who is the famous poet who wrote about the working-class life in Chicago?

52. Which is the oldest baseball park in Chicago?

53. What massive sporting and concert venue is located in Chicago?

54. Which famous explorers started their expedition in Chicago in 1673?

55. What Chicago-based television show features a satirical look at news, politics, and current events?

56. What famous candy is known for being manufactured in Chicago?

57. What is the name of the large, green park located in downtown Chicago?

58. What Chicago riverwalk offers walking, jogging, sightseeing, and even kayaking opportunities?

59. What is the name of the famous Chicago theater that opened in 1921?

60. What public art piece in Chicago was created by Pablo Picasso?

61. Which famous architect designed the Robie House in Chicago?

62. Which skyscraper in Chicago was designed by Ludwig Mies van der Rohe?

63. What Chicago music festival takes place in Union Park every summer?

64. Which artist painted the large mural in the Chicago Cultural Center titled ‘The World’s Fair Mural’?

65. Which astronaut, the second American to orbit the Earth, was born in Chicago?

66. What prestigious award is given out annually by the University of Chicago?

67. Which famous author and Nobel laureate lived in Chicago and often wrote about the city?

68. Which children’s museum is located on Navy Pier in Chicago?

69. Which famous Chicagoan was the first woman to win the Nobel Peace Prize?

70. What is the name of the event in which cows were decorated and displayed throughout Chicago in 1999?

71. What is the name of the renowned research library in Chicago?

72. Who was the first non-indigenous settler in Chicago?

73. What is the popular waterfront that stretches from the Chicago River in the south to Hollywood Beach in the north?

74. Which film, starring John Cusack and Jack Black, is set in a fictional Chicago record store?

75. What popular Chicago radio station is known for its music variety and listener participation?

76. What is the famous comedy club that originated in Chicago?

77. What dessert, first created in 1893 in Chicago, is a type of sponge cake with a custard filling?

78. What major cultural event, taking place in Grant Park, brings in artists and food from around the world?

79. What famous Chicago street runs 24 miles through the city, crossing the river twice?

80. What Chicago university is home to one of the world’s most prestigious medical schools?

81. Who was the founder of McDonald’s, the world’s largest fast-food franchise, and lived in Chicago?

82. What bird is depicted in the seal of the city of Chicago?

83. What is the name of the Chicago cultural institution dedicated to the art of improvisational comedy?

84. Which television series about a dysfunctional family is set in Chicago’s South Side?

85. What is the name of the long, skinny park that runs for 2.7 miles through downtown Chicago?

86. Which popular tourist attraction in Chicago offers a 360-degree view of the city’s skyline?

87. Who was the first European to record the site of the current city of Chicago?

88. What is the oldest public building in Chicago?

89. Which crime drama television series is set in the Chicago Police Department?

90. What is the name of the elevated train system that serves the city of Chicago?

91. Which major U.S. airline has its headquarters in Chicago?

92. What is the largest island within the city limits of Chicago?

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