Chicago Trivia

Welcome to our Chicago Trivia blog! If you're fascinated by the Windy City and want to test your knowledge of all things Chicago, you've come to the right place.

Our trivia quiz covers everything from the city's rich history and famous landmarks to its sports teams, culture, and cuisine. Whether you're a lifelong resident, a frequent visitor, or simply curious about one of America's most iconic cities, our questions will challenge you and help you discover new facts about the vibrant and diverse world of Chicago.

So, get ready to take on our ultimate Chicago Trivia challenge and see how much you really know about this amazing city!

For more quizzes, see our trivia quiz sitemap.

Chicago Trivia Questions

1. What is the nickname for Chicago?

2. Which Chicago street is known for its high-end shops and designer boutiques?

3. What is the name of the Chicago Cubs' home stadium?

4. What famous public art installation is located in Chicago's Millennium Park?

5. What Chicago-based architect designed the Sears Tower (now known as Willis Tower)?

6. In which Chicago neighborhood is the historic Wrigley Field located?

7. Which Chicago museum is home to the largest collection of Impressionist paintings outside of Paris?

8. What is the name of the famous deep-dish pizza restaurant chain founded in Chicago?

9. What famous criminal mastermind was famously incarcerated in Chicago's Alcatraz prison?

10. What famous Chicago blues musician was known as the "King of the Blues"?

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

12. What famous Chicago event is held every year on St. Patrick's Day?

13. What Chicago park is home to the Buckingham Fountain?

14. What is the name of the world-famous comedy theater in Chicago that has launched the careers of many famous comedians?

15. What is the name of the iconic Chicago theater that is home to the Joffrey Ballet and hosts many Broadway shows?

16. What is the name of the famous Chicago street that is home to the city's theater district?

17. Which famous Chicago-born playwright wrote the Pulitzer Prize-winning play "August: Osage County"?

18. Which Chicago-based basketball team has won six NBA championships in the past two decades?

19. What is the name of the famous Chicago-born chef who hosts the show "Top Chef"?

20. What is the name of the Chicago-based newspaper known for its investigative journalism?

21. Which Chicago street is famous for its high-end shopping and luxury boutiques?

22. What is the name of the famous Chicago deep-dish pizza chain that was founded in 1943?

23. Who is the famous architect behind the design of Willis Tower (formerly known as Sears Tower)?

24. What is the name of the Chicago baseball team that has won three World Series titles, the last one being in 2005?

25. What is the name of the Chicago lakefront park that is home to many famous museums, including the Field Museum and the Shedd Aquarium?

26. Which Chicago landmark was built for the 1893 World's Columbian Exposition and is now one of the most popular tourist attractions in the city?

27. Which Chicago-born musician is known as the "Queen of Soul"?

28. What is the name of the Chicago-based fast food chain that is famous for its Italian beef sandwiches?

29. Which famous Chicago movie features the line "They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue"?

30. Which famous Chicagoan was the host of the popular daytime talk show "The Oprah Winfrey

Chicago Trivia Answers

1. The Windy City
2. Michigan Avenue
3. Wrigley Field
4. The Bean
5. Fazlur Rahman Khan
6. Wrigleyville
7. The Art Institute of Chicago
8. Giordano's
9. Al Capone
10. Muddy Waters
11. The Chicago River
12. The St. Patrick's Day Parade
13. Grant Park
14. The Second City
15. The Auditorium Theatre
16. State Street
17. Tracy Letts
18. The Chicago Bulls
19. Stephanie Izard
20. The Chicago Tribune
21. Michigan Avenue (also known as "The Magnificent Mile")
22. Lou Malnati's
23. Skidmore, Owings & Merrill (SOM)
24. Chicago White Sox
25. Grant Park
26. The Ferris Wheel at Navy Pier
27. Aretha Franklin
28. Portillo's
29. The Untouchables
30. Oprah Winfrey