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50 Intriguing Chicago Trivia Questions and Answers

Reviewed by Kenton, Chief Editor·Updated May 2025·6 min read

Delve into our Chicago Trivia! With the rich tapestry of Chicago, a city renowned for its architectural marvels, historic events, and vibrant arts scene.

Chicago Trivia

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

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

  3. 3In which year was the Great Chicago Fire?

  4. 4Which body of water is Chicago located beside?

  5. 5What popular style of pizza originated in Chicago?

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

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

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

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

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

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

  12. 12What is Chicago's professional baseball team?

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

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

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

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

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

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

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

  20. 20What annual event dyes the Chicago River green?

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

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

  23. 23In which year was Chicago officially founded?

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

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

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

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

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

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

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

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

  32. 32Which fictional wizard detective calls Chicago his home?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Answer Key

  1. 1. The Windy City
  2. 2. Frank Lloyd Wright
  3. 3. 1871
  4. 4. Lake Michigan
  5. 5. Deep dish pizza
  6. 6. Al Capone
  7. 7. 4
  8. 8. Oprah Winfrey
  9. 9. The World's Columbian Exposition
  10. 10. O'Hare International Airport
  11. 11. Cracker Jack
  12. 12. Chicago Cubs
  13. 13. Willis Tower
  14. 14. Millennium Park
  15. 15. Mars Wrigley Confectionery
  16. 16. Chicago River
  17. 17. The Field Museum
  18. 18. Wrigleyville
  19. 19. Chicago White Sox
  20. 20. St. Patrick's Day celebration
  21. 21. University of Chicago
  22. 22. A bull
  23. 23. 1833
  24. 24. Navy blue
  25. 25. Lincoln Park Zoo
  26. 26. Da Bears
  27. 27. The Blues Brothers
  28. 28. Phoenix and an infant
  29. 29. Lollapalooza
  30. 30. The Second City
  31. 31. Barack Obama
  32. 32. Harry Dresden
  33. 33. Grant Park
  34. 34. The original Ferris Wheel
  35. 35. Taste of Chicago
  36. 36. Michigan Avenue
  37. 37. Tracy Letts
  38. 38. First controlled nuclear chain reaction
  39. 39. Willis Tower
  40. 40. The first major air race
  41. 41. Chicago School
  42. 42. L. Frank Baum
  43. 43. It's untitled and abstract
  44. 44. Chicago Theatre
  45. 45. Dragged Through the Garden
  46. 46. The Great Chicago Fire
  47. 47. Michelle Obama
  48. 48. Cloud Gate (or 'The Bean')
  49. 49. 360 Chicago
  50. 50. Hillary Clinton

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