130+ Chicago Trivia Quiz Questions and Answers

Chicago is home to amazing food, innovation, and fascinating history. Flowing through Chicago is the Chicago River which is the only river in the world that flows backward. A reversal technique intended to help divert the sewage away from Lake Michigan’s water supply.

Chicago is not only the largest city in the state of Illinois, but it is also the third most populated city in the U.S. Its population is only preceded by New York and Los Angeles. Take the quiz to find out the current population of Chicago.

Chicago Facts Trivia Quiz Questions and Answers

This city is also known as the “Home of the Skyscraper” since the concept of constructing tall buildings developed here, and now, Chicago is home to 4 of the country’s 10 tallest buildings.

Technological advancements in television allowed people in 1960 to stream the Presidential Debate between Richard Nixon and John F. Kennedy from the comfort of their homes. It was broadcast on Chicago’s CBS channel.

Keep scrolling to see how well you can answer this Chicago trivia!

1. Chicago, Illinois is located at the south end of which of the five US Great Lakes?

Lake Michigan


2. In which US state is Chicago located?



3. What well-known dictator donated the Balbo Monument, which was erected to commemorate the first transatlantic crossing of the Italian air force from Orbetello, Italy to Chicago, Illinois?


4. Which system of rivers and canals runs through Chicago?

Chicago River


5. Running beneath Chicago’s Uptown neighborhood are tunnels. These tunnels are infamous for their use in the jazz age as an escape route for gangsters such as Al Capone. Under which Uptown destination can you find the entrance to these tunnels?

The Green Mill


6. What is the nickname of Chicago?

The Windy City


7. One of the most famous landmarks in Chicago, this fabled structure survived the Great Fire.

The Chicago Water Tower


8. Who said “Da pleece aren’t here to create disorder, They’re here to preserve disorder”.’

Richard J. Daley


9. What is the tallest building in Chicago?

Willis Tower


10. The famous northside jazz bar was haunted by Hollywood stars and the ultimate gangster in Chicago. What is the name of this jazz bar?

The Green Mill


11. What type of pizza is Chicago famous for?

Deep Dish


12. Which sport is played at Wrigley Field?



13. Which of these items is not attached to the harness?

Whip Socket


14. What is the name given to someone who live in Chicago?



15. Being settled near a US Great Lake enabled Chicago to become one of the largest and most prosperous cities in the world, in much part because of what?

Waterway transportation


16. What type of seeds is on the bun of a classic Chicago-style hot dog?

Poppy seed


17. The University of Chicago campus has a large, bulbous, bronze sculpture by Henry Moore. It marks the site where what scientific phenomenon was first developed and tested?


18. Who is the main female character in the musical Chicago?

Roxie Hart


19. Beneath the streets of Chicago’s Loop you will find the remains of a massive underground system that served the city’s largest buildings from 1906 to 1959. What was carried through these tunnels?

Coal, mail and people on tiny trains


20. Which county is Chicago the seat of?

Cook countys


21. Completed in 1969, this 100-story steel and glass skyscraper is named after a famous American revolutionary.

The John Hancock Center


22. How many people live in Chicago (+/- 200,000)?

2.716 million


23. The famous jazz saxaphonist Fred Anderson owns this jazz joint.

The Velvet Lounge


24. True or False – Chicago is not the windiest city in the United States.



25. In 1871, most of Chicago was destroyed in the Great Chicago Fire. Out of the ashes citizens recreated the town, earning which nickname? Hint: “Phoenix” was already taken.

Second City


26. For which occasion is the Chicago River dyed in green?


27. What Chicago landmark is located at 2325-2333 N. Clark Street, where two pharaohs stand guarding a gilded entryway?

Reebie Storage & Moving Company


28. True or false – Chicago is the third most populous city in the United States?



29. What major event in the history of science occurred in an underground racquetball court at the University of Chicago in 1942?

The first self-sustaining, synthetic nuclear reaction


30. What music genre can be ‘Chicago style’?



31. Elwood Blues listed this famous structure located at 1060 W. Addison as his place of residence on his driver’s license in the movie “The Blues Brothers”.

Wrigley Field


32. Which Chicago hockey team won the Stanley Cup in 2015?

Chicago Blackhawks


33. Where do “Da Bears play?

Soldier field


34. True or False – the flow of the Chicago River was reversed.



35. This Hyde Park bar had five Ph.Ds tending bar once. You can also find the complete works of William Shakespeare and an encyclopedia.

Jimmy’s Woodlawn Tap


36. Chicago is home to the largest food festival in the world. What is it called?

Taste of Chicago food festival


37. Which word is a common command to tell your horse to trot?



38. What is the largest park in Chicago?

Lincoln Park


39. John G. Shedd was a stock boy who made his way to president of a Chicago department store. In 1924, he envisioned a salty and world-class scientific and educational museum to be called the Shedd what?



40. True or False – Chicago Riverwalk is less than 2 miles long.

True, it’s 1.25 mile


41. Which film featured a suburban Chicago sculpture, “The Spindle”, composed of eight cars skewered on a pole?


42. Which chocolate cake was created at the Palmer House Hotel in Chicago in 1893?

The Brownie


43. You may have seen Chicago’s double-decker Wacker Drive featured in “The Blues Brothers” or “Batman Begins.” Many have heard of “Upper Wacker” and “Lower Wacker,” but for a short span there is actually a third, even deeper level! What is this lowest level of Wacker Drive called?

Lower Lower Wacker


44. In which park is the Cloud Gate sculpture?

Millennium Park


45. What is “Da Loop”?



46. In which neighbourhood is Navy Pier?



47. What sport do the Chicago Cubs play?



48. This famous bar goes back to the repeal of Prohibition.

Burwood Tap


49. Greater Chicagoland extends into two other states. Which ones?

Wisconsin and Indiana

50. If I live in Cicero near Austin and Roosevelt, and I want to get to O’Hare airport, how many train lines do I have to take?



51. Who designed the Jay Pritzker Pavilion?

Frank Gehry


52. In which building can you find the observation deck 360 Chicago?

John Hancock Building


53. One of the oldest zoos in the US, the Chicago Lincoln Park Zoo protects a massive “Quercus macrocarpa”, which is what? Definitely its bark is worse than its bite.

Burr oak tree


54. In the late 1970s, Chicagoan Mitch Szewczyk began to decorate the exterior of his home with what items for protection and as a tribute to public figures he admired?



55. Which ​​golden sponge cake with a creamy filling was created in Chicago?



56. The Great Fire of Chicago destroyed what major landmark, formerly located at the corner of Ontario Street and McClurg Court in the area now known as Streeterville? (Hint: remember the theme!)

Nothing–there was no land there during the Great Fire.


57. The first televised presidential debate took place in Chicago. Who were the two candidates?

Kennedy and Nixon


58. Is Jacques Cousteau your hero? At this site you can imagine you are him and explore the world beneath the waves.

The John G. Shedd Aquarium


59. In which museum can you see the painting American Gothic by Grant Wood?

Art Institute of Chicago


60. What was Riverview?

Amusement park


61. True or false – The first US blood bank was established in Chicago.



62. Which Chicago classic has a stone Schlitz globe on its roof?

Bamboo Lounge


63. The first open-heart surgery was performed in Chicago. Who was the surgeon?

Daniel Hale Williams


64. Which line heads up through Evanston to serve Northwestern University?



65. What is the largest library in Chicago?

Harold Washington Library Center


66. What movie studio that produced films starring Charlie Chaplin, Gloria Swanson and Wallace Beery is located on W. Argyle Street in Chicago, IL?

Essanay Studios


67. Which US President was a community organizer in Chicago in the 80s?


68. Chicago can be loosely divided into four major areas – the Loop, the North Side, the West Side and the South Side. The South side is by far the largest area of the city, stretching from just beneath the Loop all the way down to the Indiana border. Where does the Loop end and the South Side begin?

Roosevelt Road


69. How many major league sports are there in Chicago?



70. This structure was originally intended for use in shipping and entertainment. It has seen many uses over the years, but as of 1994 it is almost exclusively used for entertainment.

Navy Pier


71. Eccentric Lar Daly unsuccessfully ran for mayor several times in Chicago. What was his nickname?

America First


72. How many parks are there in Chicago?



73. Lincoln Park is a yuppie enclave on the near north side, and “Trixies” is a nickname for its inhabitants. Which of the following is a line that Lincoln Park Trixies can take to work downtown?



74. How many miles of bike lanes are there in Chicago?



75. Aside from the antique horse trough still in use at Water Tower Park, there is another on Michigan Avenue. At which cross street?



76. How many Michelin-starred restaurants are there in Chicago?



77. A famous place to visit in Chicago is the Willis Tower, the tallest building in the world for 23 years. What was the original name of this lofty building?

Sears Tower


78. In which Chicago park does the music festival Lollapalooza take place?

Grant Park


79. Name the river that is in Chicago.

Illinois River


80. Chicago had seven mayors between 1955 and 2004, During how many of those 49 years was the mayor’s name Daley?



81. _________ gallons of water soar to heights up to 150 feet every minute at Buckingham Fountain in Grants Park.

14,000 gallons


82. You can go here to get the most up-to-date bulletins on the El schedules and routes.

The Time out Chicago


83. The name “Chicago” comes from the Native American name “Chicagoua,” meaning _______.

The place of the wild onion


84. This famous high school was designed by Royer, Danley and Smith, with frescoes by Edgar Britton. This school is actually in a suburb of Chicago. This is one of Illinois designated historic places.

Bloom High School


85. After the fire, __________ donated books to the people of Chicago.


86. Which Chicago area places would I ride the Orange line to?

Midway Airport


87. ___________ Native American people were driven from Chicago area after 1830.



88. ________ police officers were killed at Haymarket Square in the 19th century’s most sensational labor incident.



89. From the elevated train you can see into the carriage yard of the oldest continuously operating barn in the city. Which line?



90. At which popular Chicago museum can you make a giant heart beat in time to yours, or get a virtual instructor to take note of your basketball moves?

Museum of Science and Industry


91. In 1889, mark the new Chicago landmark that was the largest building in the world.

The Auditorium


92. If you don’t fear the reaper, you can visit what inventor of the Harvesting Machine at Chicago’s Graceland Cemetery?

Cyrus McCormack


93. What is Chicago’s population?

2.71 million


94. Chicago’s version of the Champs-Elysées.

The Magnificent Mile


95. What is the name of the restaurant in which a doctoral student at the University of Chicago wrote his dissertation on?

Valois Cafeteria


96. What is considered a must when you visit Chicago for the first time?

You must take a stroll through the downtown for a mini tour of the history of the high-rise.


97. One Saturday, a Northwestern student, who lives on campus in Evanston, would like to go visit his friend who is studying and living at IIT (the Illinois Institute of Technology) on the near South Side. What is a reasonable series of trains for him to take?

Purple to Red to Green


98. How many people both foreign and domestic visited Chicago in 2008?

Chicago had 45.6 million visitors in 2008.


99. At what street corner do all address numbers originate from in Chicago?

Corner of State and Madison streets

100. Covering more than 50 acres (20 hectares) of shore front, Chicago’s Navy Pier extends out into the lake. What do tourists find there?

Shops and rides


101. What is the popular name for the heart of Chicago’s downtown business district?

The Loop


102. Millennium Park in downtown Chicago has been a major tourist draw since its opening in 2004. What lies underneath the Park?

Parking garage


103. When you travel to Chicago, how should you prepare to dress?

Prepare to dress in layers.


104. Although the New York Stock Exchange is much more famous, this is the world’s first publicly traded financial exchange.

Chicago Mercantile Exchange


105. What is your best bargain for getting from O’Hare International Airport to downtown Chicago?

Blue Line on the El


106. This building which was built in 1872 (one year after the great Chicago fire) is home to some of the greatest jazz in the city.

The Green Door Tavern


107. What should you know in order to keep a reference when locals give you directions?

When travelling north Lake Michigan is on your right and going south it is on your left.


108. How many Western Avenue stations are there, on all train lines?



109. Where can you go to get the most up-to-date bulletins on the El schedules and routes?

The Time out Chicago


110. The Chicago Field Museum features one of the world’s largest, most complete, and best preserved skeletons. Named Sue, which exhibit greets you at the door? ““Jurassic Park” had one.


111. What is the best way to reach the city’s main museums, along with some great restaurants in downtown Chicago?

Walk from one to another it is easy and you are doing your body a favor.


112. Which Chicago suburb museum features information and displays about Ecuadorian blow darts, laughing gas, and acupuncture needles?

Wood Library – Museum of Anesthesiology


113. What can someone who loves music do in Grant Park in June?

Grant Park is the site of the Chicago Blues Festival featuring free outdoor concerts.


114. What is special about Lincoln Park Zoo that you will rarely find anywhere else?

No admission fee


115. Originally built as the city’s library, this historic structure is now known as the “People’s Palace”.

Chicago Cultural Center


116. What do we fondly refer to our “neighbors to the north” in Wisconsin as?



117. Finally, since I am a die hard White Sox I need one question that relates to the Sox. If I’m leaving Comiskey after a White Sox winner which restaurant would serve me Chicken Carlos?

Bertucci’s Corner


118. With an estimated completion date of 2019, the Deep Tunnel project is a major civic works program that started underneath Chicago and its surrounding areas in the 1970s. What is the purpose of this project?

Reducing flooding and preventing the buildup of sewage in Lake Michigan


119. Want to learn about your environment and how to conserve it while having fun? Go here.

The Notebaert Nature Museum


120. What is Chicago?

Chicago is the most populous city in the U.S. state of Illinois.


121. Famous for its Picasso sculpture outside, it is also featured prominently in the movie “The Blues Brothers”.

Richard Daley Center


122. Many utility lines run underneath the Chicago – water, gas, electric and telephone lines can all be found down there. However, only one of those systems is controlled entirely by the city government. Which utility department is manned entirely by the city?



123. With a population of 2,746,388 in the 2020 census, it is also the most populous city in what area?

The Midwestern United States and the fifth most populous city in North America.


124. This building is famous for its association with a gangster and Hollywood.

Biograph Theater


125. The Chicago area has one of the highest gross domestic products (GDP) in the world, generating how much in 2018?

$689 billion


126. The economy of Chicago is diverse, with no single industry employing more than what percentage of the workforce?



127. The city has had several nicknames throughout its history, such as what?

The Windy City, Chi-Town, Second City, and City of the Big Shoulders.


128. Summers are hot and humid, with frequent what?

Heat waves


129. In a normal summer, temperatures reach at least 90 °F (32 °C) on how many days?

As many as 23 days.


130. How many domestic business travelers?

11.09 million.


131. Chicago is the United States’ third largest what?

Convention destination.


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