50 Intriguing Chicago Trivia Questions and Answers

Delve into our Chicago Trivia! With the rich tapestry of Chicago, a city renowned for its architectural marvels, historic events, culinary delights, and vibrant arts scene. This collection of trivia touches on various facets of the Windy City. Whether you’re a native Chicagoan, a fervent fan of its lore, or someone with a newfound interest, test your knowledge and discover something new about one of America’s most iconic cities. Let’s see how well you know Chicago Trivia!

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Chicago Trivia

1. What is Chicago commonly referred to as, based on its weather conditions?

2. Which famous American architect made Chicago his home and designed many buildings there?

3. In which year was the Great Chicago Fire?

4. Which body of water is Chicago located beside?

5. What popular style of pizza originated in Chicago?

6. Which notorious gangster was synonymous with Chicago during the Prohibition era?

7. How many stars are on the Chicago city flag?

8. Which famous talk-show host made Chicago the home of her studio for many years?

9. Which world’s fair was held in Chicago in 1893?

10. What is the name of Chicago’s primary airport?

11. Which popular candy was invented in Chicago in 1893?

12. What is Chicago’s professional baseball team?

13. What is the tallest building in Chicago as of 2021?

14. Which Chicago park is home to attractions like Cloud Gate and Crown Fountain?

15. Chicago is home to the headquarters of which major candy company?

16. What is the name of the river that runs through Chicago?

17. Which Chicago museum has Sue, the largest and most complete T. rex ever found?

18. In which neighborhood can you find Chicago’s historic Wrigley Field?

19. Which major league baseball team plays at Guaranteed Rate Field?

20. What annual event dyes the Chicago River green?

21. Which Chicago university is known for its economics and business programs?

22. What animal is depicted in the Chicago Bulls logo?

23. In which year was Chicago officially founded?

24. What is the primary color of the Chicago Bears’ jersey?

25. Which zoo, one of the oldest in the US, can be found in Chicago?

26. Which long-running SNL sketch features superfans of the Chicago Bears?

27. Which 1980 movie showcased the comedic talents of two ‘brothers’ on a mission in Chicago?

28. What two animals are featured on the Chicago city seal?

29. Which large music festival takes place in Chicago’s Grant Park every summer?

30. Which Chicago theater is famed for its comedy and has been a launch pad for numerous comedic talents?

31. Which president-elect gave his victory speech in 2008 in Chicago’s Grant Park?

32. Which fictional wizard detective calls Chicago his home?

33. In which park is the Chicago Art Institute located?

34. Which Ferris wheel, showcased in 1893, was a marvel of its time?

35. What Chicago festival celebrates the culinary arts with numerous food vendors?

36. Chicago’s Magnificent Mile is primarily located on which avenue?

37. Which Pulitzer-prize winning playwright wrote ‘August: Osage County’ while living in Chicago?

38. Which major scientific achievement happened at the University of Chicago in 1942?

39. Which Chicago landmark offers views from its Skydeck at 1,353 feet?

40. In 1924, which aviation event began in Chicago and ended in Los Angeles?

41. What style of architecture is the Rookery Building a prime example of?

42. Which famous children’s book author was born in Chicago in 1900?

43. What unique feature does the Chicago Picasso sculpture in Daley Plaza have?

44. Which historic Chicago theater is known for its iconic marquee and has hosted numerous concerts?

45. What is the nickname for the traditional Chicago-style hot dog, free from ketchup?

46. Chicago’s Water Tower is one of the few structures to survive which event?

47. Which former First Lady was born in Chicago in 1964?

48. What unique structure was built for Chicago’s 2004 Millennium Park?

49. Which Chicago attraction offers a 360-degree view of the city and includes TILT, a thrilling tilt-outward experience?

50. Which former US Secretary of State grew up in the Chicago suburb of Park Ridge?