1. What is Chicago’s nickname?
A) The Big Apple
B) The Windy City
C) The Motor City
D) The Mile-High City
Answer: B) The Windy City
2. Which lake borders Chicago to the east?
A) Lake Superior
B) Lake Michigan
C) Lake Huron
D) Lake Erie
Answer: B) Lake Michigan
3. Which river flows through downtown Chicago?
A) Mississippi River
B) Chicago River
C) Des Plaines River
D) Fox River
Answer: B) Chicago River
4. Which Chicago park is home to the famous sculpture “The Bean”?
A) Grant Park
B) Millennium Park
C) Lincoln Park
D) Jackson Park
Answer: B) Millennium Park
5. What is the official name of “The Bean” sculpture?
A) Silver Orb
B) Cloud Gate
C) Sky Mirror
D) Reflective Sphere
Answer: B) Cloud Gate
6. What is the name of Chicago’s iconic skyline building formerly known as the Sears Tower?
A) John Hancock Center
B) Willis Tower
C) Trump Tower
D) Aon Center
Answer: B) Willis Tower
7. What famous Chicago food item is known for its deep crust and thick layers of cheese and toppings?
A) Hot Dog
B) Italian Beef Sandwich
C) Deep-Dish Pizza
D) Chicago-style Popcorn
Answer: C) Deep-Dish Pizza
8. Which Chicago museum is known for its extensive collection of Impressionist and Post-Impressionist paintings?
A) The Art Institute of Chicago
B) The Field Museum
C) Museum of Contemporary Art Chicago
D) Shedd Aquarium
Answer: A) The Art Institute of Chicago
9. What famous route begins in Chicago and stretches to Santa Monica, California?
A) Route 20
B) Route 30
C) Route 66
D) Route 1
Answer: C) Route 66
10. What is the name of Chicago’s professional basketball team?
A) Chicago Bears
B) Chicago Cubs
C) Chicago Blackhawks
D) Chicago Bulls
Answer: D) Chicago Bulls
11. Which famous Chicago zoo is located within Lincoln Park?
A) Brookfield Zoo
B) Lincoln Park Zoo
C) Shedd Zoo
D) Garfield Park Zoo
Answer: B) Lincoln Park Zoo
12. What is the name of the Chicago neighborhood known for its vibrant Mexican-American culture?
A) Chinatown
B) Little Italy
C) Pilsen
D) Ukrainian Village
Answer: C) Pilsen
13. Which Chicago airport is one of the busiest in the world?
A) Midway International Airport
B) O’Hare International Airport
C) Gary/Chicago International Airport
D) Rockford International Airport
Answer: B) O’Hare International Airport
14. Which famous Chicago event involves dyeing the Chicago River green?
A) Independence Day
B) St. Patrick’s Day
C) Memorial Day
D) Halloween
Answer: B) St. Patrick’s Day
15. What is the name of the Chicago baseball team that plays at Wrigley Field?
A) Chicago White Sox
B) Chicago Cubs
C) Chicago Blackhawks
D) Chicago Bears
Answer: B) Chicago Cubs
16. What is the name of the observatory deck located in the Willis Tower?
A) The Edge
B) The Lookout
C) The Ledge
D) The Skywalk
Answer: C) The Ledge
17. Which Chicago neighborhood is known as a hub for jazz and blues music?
A) Wicker Park
B) Hyde Park
C) Bronzeville
D) River North
Answer: C) Bronzeville
18. Which Chicago museum is home to the famous T. rex skeleton known as “Sue”?
A) The Field Museum
B) The Art Institute of Chicago
C) Museum of Science and Industry
D) Adler Planetarium
Answer: A) The Field Museum
19. Which famous Chicago landmark is known for its reflective “Crown Fountain”?
A) Navy Pier
B) Millennium Park
C) Grant Park
D) Maggie Daley Park
Answer: B) Millennium Park
20. Which Chicago street is famous for its high-end shopping and luxury boutiques?
A) Michigan Avenue
B) State Street
C) Randolph Street
D) Wabash Avenue
Answer: A) Michigan Avenue
21. What is the name of the Chicago neighborhood that is home to Wrigley Field?
A) Lincoln Park
B) Lakeview
C) Wrigleyville
D) Old Town
Answer: C) Wrigleyville
22. Which Chicago theater is known for being the birthplace of improvisational comedy?
A) The Second City
B) Steppenwolf Theatre
C) Goodman Theatre
D) Chicago Theatre
Answer: A) The Second City
23. What is the name of the largest science museum in Chicago?
A) Museum of Science and Industry
B) The Field Museum
C) Adler Planetarium
D) Shedd Aquarium
Answer: A) Museum of Science and Industry
24. What iconic Chicago event takes place along the shore of Lake Michigan and features air and water performances?
A) Chicago Air and Water Show
B) Taste of Chicago
C) Lollapalooza
D) Chicago Marathon
Answer: A) Chicago Air and Water Show
25. Which Chicago building is known for its X-shaped external supports?
A) Willis Tower
B) John Hancock Center
C) Aon Center
D) Tribune Tower
Answer: B) John Hancock Center
26. Which Chicago neighborhood is known for its historic mansions and the University of Chicago?
A) Wicker Park
B) Logan Square
C) Hyde Park
D) Lincoln Square
Answer: C) Hyde Park
27. Which Chicago museum focuses on astronomy and space science?
A) Adler Planetarium
B) Shedd Aquarium
C) The Field Museum
D) Museum of Science and Industry
Answer: A) Adler Planetarium
28. Which Chicago river is famously dyed green for St. Patrick’s Day celebrations?
A) Des Plaines River
B) Calumet River
C) Chicago River
D) Fox River
Answer: C) Chicago River
29. Which Chicago street is known as the birthplace of the modern skyscraper?
A) LaSalle Street
B) Wabash Avenue
C) State Street
D) Michigan Avenue
Answer: A) LaSalle Street
30. What is the name of the oldest ballpark in Chicago?
A) Guaranteed Rate Field
B) Wrigley Field
C) Soldier Field
D) Comiskey Park
Answer: B) Wrigley Field
31. Which Chicago neighborhood is famous for its Polish heritage and cuisine?
A) Greektown
B) Chinatown
C) Wicker Park
D) Avondale
Answer: D) Avondale
32. Which Chicago neighborhood is known for its large concentration of art galleries?
A) River North
B) Pilsen
C) Wicker Park
D) South Loop
Answer: A) River North
33. What Chicago landmark is known for its gothic architecture and once housed the Chicago Tribune?
A) Tribune Tower
B) Water Tower Place
C) Merchandise Mart
D) Marina City
Answer: A) Tribune Tower
34. Which Chicago institution is known for its significant collection of American Gothic and other American art?
A) The Art Institute of Chicago
B) The Field Museum
C) Museum of Contemporary Art Chicago
D) Smart Museum of Art
Answer: A) The Art Institute of Chicago
35. What is the name of the iconic theater on State Street with a famous marquee?
A) Chicago Theatre
B) Oriental Theatre
C) Cadillac Palace Theatre
D) Goodman Theatre
Answer: A) Chicago Theatre
36. Which Chicago neighborhood is known for its German heritage and annual Oktoberfest celebrations?
A) Lincoln Square
B) Humboldt Park
C) Uptown
D) Bridgeport
Answer: A) Lincoln Square
37. What is the name of the observatory deck located in the John Hancock Center?
A) Skydeck
B) The Ledge
C) 360 Chicago
D) The Edge
Answer: C) 360 Chicago
38. Which Chicago park is known for its vast green spaces and the Lincoln Park Zoo?
A) Millennium Park
B) Grant Park
C) Lincoln Park
D) Jackson Park
Answer: C) Lincoln Park
39. Which Chicago river was famously reversed in the 19th century for sanitation purposes?
A) Chicago River
B) Des Plaines River
C) Calumet River
D) Fox River
Answer: A) Chicago River
40. Which Chicago neighborhood is known for its historic architecture and tree-lined streets?
A) Wicker Park
B) Lincoln Park
C) Old Town
D) River North
Answer: C) Old Town
41. What is the name of the tallest residential building in Chicago?
A) Trump Tower
B) Aqua Tower
C) One Bennett Park
D) Vista Tower
Answer: A) Trump Tower
42. Which Chicago festival is known for its diverse music lineup and takes place in Grant Park?
A) Lollapalooza
B) Pitchfork Music Festival
C) Chicago Blues Festival
D) Chicago Jazz Festival
Answer: A) Lollapalooza
43. What Chicago street is known for its vibrant nightlife and music scene?
A) Halsted Street
B) State Street
C) Michigan Avenue
D) Wells Street
Answer: A) Halsted Street
44. Which Chicago building is famous for its art deco architecture and was once the tallest building in the world?
A) Willis Tower
B) Tribune Tower
C) Chicago Board of Trade Building
D) Aon Center
Answer: C) Chicago Board of Trade Building
45. What is the name of Chicago’s premier public art event that takes place annually?
A) Chicago Artists Month
B) Chicago Open Air
C) Chicago SummerDance
D) Chicago Air and Water Show
Answer: A) Chicago Artists Month
46. Which Chicago museum is known for its immersive exhibits and interactive displays?
A) Museum of Science and Industry
B) The Field Museum
C) Shedd Aquarium
D) Adler Planetarium
Answer: A) Museum of Science and Industry
47. What is the name of the annual food festival that takes place in Chicago, showcasing local cuisine?
A) Chicago Gourmet
B) Taste of Chicago
C) Chicago Food & Wine Festival
D) Chicago Restaurant Week
Answer: B) Taste of Chicago
48. Which Chicago neighborhood is known for its LGBT-friendly culture and events?
A) Andersonville
B) Lakeview
C) Boystown
D) Pilsen
Answer: C) Boystown
49. What is the name of the popular Chicago lakefront path for walking, running, and biking?
A) Lakefront Trail
B) Chicago Riverwalk
C) The 606
D) Millennium Park Path
Answer: A) Lakefront Trail
50. Which Chicago landmark features a “light tower” that lights up the night sky?
A) Willis Tower
B) John Hancock Center
C) Navy Pier
D) Tribune Tower
Answer: C) Navy Pier