250+ Best Chicago Trivia Questions and Answers (Easiest to Hardest)

Chicago Trivia

Chicago, the Windy City, is a metropolis with a rich history, stunning architecture, and a unique cultural scene. Chicago Wednesday Trivia Night games are often a fantastic way to chill while testing your Windy City knowledge.

If you wish to win at Bar Trivia Chicago game this week, now is the perfect time to get acquainted with possible questions that will be thrown at you. I have curated an extensive list of questions and answers often used for Chicago Trivia games across trivia hosts in the Windy City.

Learn the rules of the game and answer all correctly to emerge the champion.

Can you hire someone to do bar trivia in Chicago?

Hiring someone to do bar trivia for you in Chicago is generally not allowed by the establishments hosting the trivia nights.

Since these quizzes are meant to be tests of knowledge and wit for the participating teams, having someone else answer the questions for you would defeat the purpose and be unfair to other teams.

If you are not sure of winning alone, form a team with friends or colleagues or join a trivia team at bars that have regular trivia nights.

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Bar Trivia Chicago Question and Answers

What nickname does Chicago hold for its signature gusty winds?

(Answer: The Windy City)

2. Which iconic bean sculpture graces Millennium Park?

(Answer: Cloud Gate)

3. What famous street marks the north-south division of the city?

(Answer: State Street)

4. What major sporting event takes place annually on the Chicago River?

(Answer: The Chicago Riverwalk Kayak Marathon)

5. Which renowned architect designed the Willis Tower (formerly Sears Tower)?

(Answer: Bruce Graham)

6. Deep dish or thin crust? Which style of pizza reigns supreme in Chicago?

(Answer: Deep dish)

7. What iconic hot dog chain boasts the slogan “No ketchup, no mustard, just relish”?

(Answer: Vienna Beef)

8. Which neighborhood is known for its vibrant jazz scene?

(Answer: Wicker Park)

9. What legendary blues musician hailed from Chicago?

(Answer: Muddy Waters)

10. Which university in Chicago boasts the nickname “Maroons”?

(Answer: The University of Chicago)

11. What unusual nickname did Chicago briefly hold in the 19th century?

(Answer: The Onion Patch)

12. What infamous fire reshaped the city’s landscape in 1871?

(Answer: The Great Chicago Fire)

13. Which peculiar landmark features upside-down houses and a tilted fountain?

(Answer: Tiltworld)

14. What notorious gangster was dubbed “The Public Enemy”?

(Answer: John Dillinger)

15. Which iconic theater district houses Broadway-caliber productions?

(Answer: The Loop)

16. What hidden gem park boasts a stunning view of the city skyline?

(Answer: Lincoln Park 2550)

17. Which influential architect designed the Art Institute of Chicago?

(Answer: Shepley, Rutan and Coolidge)

18. What quirky museum houses miniature replicas of world landmarks?

(Answer: The Art Institute of Chicago’s Thorne Miniature Rooms)

19. What beloved children’s book series is set in Chicago?

(Answer: Ramona Quimby)

21. Which legendary blues club hosted the likes of Muddy Waters and B.B. King?

(Answer: The Blue Chicago)

22. What lesser-known nickname references Chicago’s role in the Underground Railroad?

(Answer: The Gateway to Freedom)

23. Which historic landmark was once the tallest building in the world?

(Answer: The Tribune Tower)

24. What hidden passageway connects buildings in the Loop?

(Answer: The Pedway)

25. Which infamous serial killer terrorized Chicago in the 1990s?

(Answer: H.H. Holmes)

26. What unique architectural detail adorns the Wrigley Building?

(Answer: Terracotta terracing)

27. Which legendary radio station pioneered blues broadcasting in Chicago?

(Answer: WVON)

28. What hidden gem park features a nature sanctuary and a working farm?

(Answer: North Park Village Nature Center)

29. What iconic sculptor designed the Buckingham Fountain in Grant Park?

(Edward Buckingham)

30. Which influential architect designed the iconic Chicago bungalow style?

(Frank Lloyd Wright)

31. What beloved annual event celebrates the city’s Irish heritage?

(Answer: The Chicago St. Patrick’s Day Parade)

32. What iconic statue graces Daley Plaza, facing Buckingham Fountain? 

(Answer: Picasso’s “Eye”)

33. Which world-renowned comedy theater launched the careers of many famous comedians? 

(Answer: Second City)

34. What historic neighborhood boasts Victorian-era mansions and cobblestone streets? 

(Answer: Lincoln Park)

35. Which popular annual summer festival takes place in Grant Park? 

(Answer: Taste of Chicago)

36. What nickname references Chicago’s role as a transportation hub? 

(Answer: The Crossroads of America)

37. Which influential architect designed the Navy Pier? 

(César Pelli)

38. What hidden gem park features a lagoon and boathouse? 

(Answer: Hamlin Park)

39. Which influential architect designed the Robie House, a National Historic Landmark? 

(Frank Lloyd Wright)

40. What beloved annual event celebrates the city’s Polish heritage? 

(Answer: Dozynki Harvest Festival)

41. Which iconic musical premiered at the Shubert Theatre in 1975? 

(Answer: “A Chorus Line”)

42. What lesser-known nickname references Chicago’s role in the grain trade? 

(Answer: The Hog Butcher to the World)

43. Which historic ballpark hosted the birth of Major League Baseball in 1876? 

(Answer: DePaul Field)

44. What hidden passageway connects Millennium Park to Grant Park? 

(Answer: The BP Bridge)

45. Which notorious architect and engineer designed the infamous “H.H. Holmes Murder Castle”? 

(Answer: Daniel Burnham)

46. What unique nickname references Chicago’s connection to Lake Michigan? 

(Answer: The Second City)

47. Which renowned architect designed the stunning Shedd Aquarium? 

(Adrian Smith)

48. What hidden gem park features a butterfly house and native plant gardens? 

(Answer: Peggy Notebaert Nature Museum)

49. Which influential architect designed the iconic Rookery Building in the Loop? 

(Frank Lloyd Wright)

50. What beloved annual event celebrates the city’s LGBTQ+ community? 

(Answer: Chicago Pride Parade)

51. Which iconic rock band hails from Chicago, known for their energetic live shows? 

(Answer: Wilco)

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Random Trivia Chicago Questions and Answers

  1. Bixi, Bold Dog, Lo Rez, Saint Errant, and Half Acre are all names of what type of company located in Chicago? They are all part of an industry that has exploded in popularity across the US in the 2010s.

    Answer: Brewery
  2. What “F” Natural History Museum was established in Chicago in 1894? Designed by Daniel Burnham, it is also a word that can be used to describe an open area of land.

    Answer: Field
  3. The Chicago skyscraper still informally known by its original name, the Sears Tower, has been officially named what since 2009?

    Answer: The Willis Tower
  4. Akin to New York City’s MetroCard, what is the name of the electronic fare payment system used by the Chicago Transit Authority that launched in 2013?

    Answer: Ventra
  5. What is the name of the 2020 ESPN sports documentary miniseries that focused on Michael Jordan’s final season with the Chicago Bulls?

    Answer: The Last Dance
  6. At what baseball stadium is Ferris Bueller spotted during his titular romp though a “sick day” in the streets of Chicago?

    Answer: Wrigley Field
  7. Named after the inventor George who first constructed it at the 1893 Chicago World’s Fair, what carnival attraction could you visit this summer at the London Eye, the Singapore Flyer, or the Ain Dubai?

    Answer: Ferris Wheel
  8. The Viper at Great America in Chicago. Judge Roy Scream in Texas. The Comet at Great Escape in New York. Those are three of the wooden roller coasters the thrill seeker in your life could ride if you picked up a sextet of passes to tour the theme parks run under the, uh, banner of what company?

    Answer: Six Flags
  9. What is the name of the public park in Chicago’s Loop area? It’s not necessary to spend 1,000 years there.

    Answer: Millennium Park
  10. Let’s look backward! Today, if you visited the corner of Randolph and Carpenter in Chicago’s Near West Side, you would see the world-famous golden arches sign at McDonald’s global headquarters. From 1990 – to 2014, that was the same location the media titan filmed her titular show behind the famous Harpo Studios banner.

    Answer: Oprah Winfrey Show
  11. N Michigan Avenue in Chicago is home to what large neo-Gothic Tower, built in 1925? It gets its “T” name from the popular Chicago newspaper and media company that used to have its offices in the building.

    Answer: Tribune Tower
  12. What federation of motor clubs, known for its roadside service and its repetitive acronym, was founded in 1902 in Chicago, Illinois? It is a privately held not-for-profit national member group.

    Answer: American Automobile Association
  13. What basketball player hit a game winning shot in the 1982 NCAA championship game, securing a title win for UNC over Georgetown? He later went on to the NBA, doing even better and bigger things in Chicago.

    Answer: Michael Jordan
  14. Chicagoan Tahera Rahman became news herself in 2018, when she became the first full-time news anchor to go on air wearing what garment?

    Answer: Hijab
  15. Chicago native Jennifer Hudson won both an Oscar and a Golden Globe for her performance in what 2006 musical film?

    Answer: Dreamgirls
  16. A September 28, 2021 ceremony commemorated the breaking of ground for construction of the Barack Obama Presidential Center in what U.S. city?

    Answer: Chicago
  17. In 1988, what international food company pushed the city of Omaha into destroying a historic district so they could put up a new headquarters? In 2015, the company relocated its headquarters to Chicago.

    Answer: ConAgra
  18. Named for a major Midwestern city, what long-running Broadway musical features songs like “All That Jazz,” “Cell Block Tango,” and “Mr. Cellophane?”

    Answer: Chicago
  19. If you walked due east from the tip of Navy Pier, you’d walk into Lake Michigan. If you could walk on water and continue walking east, your first step on land would be in what US state?

    Answer: Michigan
  20. Long before he played Ethan Hunt in the “Mission: Impossible” films, what actor played a teenager who gets into trouble while his parents are away in the 1983 film “Risky Business?”

    Answer: Tom Cruise
  21. Rowr! What is the feline name of the sports teams of Northwestern University?

    Answer: Wildcats
  22. Initially launched in 2013 with 750 bikes and 75 docking stations, what is the name of Chicago’s bike-share system?

    Answer: Divvy
  23. What orthopedics brand with a blue-and-white logo was founded in 1906 by a Chicago shoemaker’s apprentice who was in medical school at the time?

    Answer: Dr. Scholl’s
  24. Which of the 8 lines on Chicago’s famed “L” system served the most passengers in 2018?

    Answer: Red Line
  25. Queen Latifah was nominated for a Best Supporting Actress Oscar for her role in “Chicago,” but lost to what costar with a hyphenated last name?

    Answer: Catherine Zeta-Jones
  26. What American director adapted the ancient Greek drama “Lysistrata” to the modern-day South Side in the 2015 film “Chi-Raq?”

    Answer: Spike Lee
  27. According to the lyrics of “Sweet Home Chicago,” “don’t you wanna go home from the land of” what U.S. state that contains one of the two cities more populous than Chicago?

    Answer: California
  28. What park and conservatory on Central Park Avenue in Chicago shares its name with the 20th US president, as well as a famous Jim Davis creation?

    Answer: Garfield Park Conservatory
  29. 1927 Film > 1975 Musical > 2002 Film. Behind Mexico City, what second most populous city in the Central Time Zone – I guess famous for “All That Jazz” – lends its name to an Oscar-winning movie?

    Answer: Chicago
  30. Anish Kapoor’s public sculpture “Cloud Gate,” installed in Chicago’s Millennium Park, is better known by what legume-y nickname?

    Answer: The Bean
  31. The Chicago Bears are oft referred to as the “Monsters of the Midway” with the Midway referring to the location of the first ever Ferris Wheel constructed during the 1893 edition of what event?

    Answer: World’s Fair
  32. Founded in 1971, what famous Chicago restaurant chain is named after its founder, who worked in the city’s very first deep-dish pizzeria in the 1940s?

    Answer: Lou Malnati’s
  33. With a time of 2 hours, 35 seconds in Chicago, Kenya’s Kelvin Kiptum became the new men’s world record holder in what race distance?

    Answer: Marathon
  34. One of the stars on Chicago’s flag commemorates what 1871 tragedy that also provided the city’s MLS team name?

    Answer: The Great Chicago Fire
  35. What is the name of the triple-A minor league baseball affiliate of the Chicago White Sox that plays its home games at Truist Field in Charlotte, North Carolina?

    Answer: Charlotte Knights
  36. What is the trademarked term that describes a section of Michigan Avenue running from the Chicago River to Oak Street?

    Answer: The Magnificent Mile
  37. Which of the Chicago “L” system’s colored lines has the fewest stations, with just three: Howard, Oakton-Skokie, and Dempster-Skokie?

    Answer: Yellow
  38. If you had tickets to see Game 3 of the 1932 World Series at Wrigley Field in Chicago, you would see a famous gesture by what famed slugger?

    Answer: Babe Ruth
  39. Willis Tower in Chicago is home to what 103 story high observation tower with clear boxes, as seen in movies such as “Ferris Bueller’s Day Off?” Its name kind of sounds like it’s part of an aerial patio.

    Answer: Skydeck
  40. In 1982, seven deaths in Chicago were attributed to an over-the-counter medication that had been laced with potassium cyanide. The murders spurred a public health investigation that brought about the “tamper-proof” packaging pill bottles have today. Which OTC pain reliever/fever-reducer was implicated in the poisonings?

    Answer: Tylenol
  41. Measured by the number of students, what is the largest college in Illinois with the word ‘Chicago’ in its full name?

    Answer: University of Illinois at Chicago
  42. Chicagoan Gwendolyn Brooks became the first African-American woman to win what literary prize in 1949?

    Answer: Pulitzer Prize
  43. North Michigan Avenue in Chicago is home to what “central” 100-floor skyscraper, funded by a life insurance company which got its name from a president of the Continental Progress with an alleged big signature?

    Answer: John Hancock Center
  44. Because of its oblong shape, Chicago’s giant metal “Cloud Gate” sculpture is nicknamed for what staple food?

    Answer: Bean
  45. What Chicago-based coffee brand has a 14-letter name that means the highly educated members of a society as a group?

    Answer: Intelligentsia
  46. Eight friends from a Chicago-area high school used a Kickstarter in 2011 to create what popular party game whose black-and-white cards feature politically incorrect fill-in-the-blanks?

    Answer: Cards Against Humanity
  47. Geese control companies like Wild Goose Chase in Chicago and Geese Police in New Jersey have pioneered strategies for “harassing” nuisance geese using what animals?

    Answer: Dogs
  48. Jordan Peele met his famous comedy partner around 2002 at Second City in Chicago, and the two eventually used their surnames as the title of a sketch comedy series. Who was this partner?

    Answer: Key
  49. Bell Labs showed off the first functional silicon solar cell in 1954 by powering a miniaturized version of what fairground ride that you’d find on Chicago’s Navy Pier?

    Answer: Ferris wheel
  50. With territory on Baranof Island, Chicagof Island, and Kruzof Island, what five-letter city in southeast Alaska has the largest land area of any city in the United States, with approximately 2,870 square miles?

    Answer: Sitka

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Hard Trivia Chicago Questions and Answer

  1. What well-known 1930 Chicago building was the first of its kind in the United States, earned its architect the gold medal of the Chicago chapter of the American Institute of Architects, was declared a National Historic Landmark in 1987, and has an official mission to inspire exploration and understanding of the universe?

    Answer: Adler Planetarium
  2. Mostly seen on a certain Chicago dish, sport peppers most likely got their name from being served during games of which sport?

    Answer: Baseball
  3. What number was the Order created by the Galactic Republic, which secretly branded all Jedi as enemies of the Republic and subject to direct execution? It is the same number as the Will Rogers Highway, a famous Route spanning from Chicago to Los Angeles.

    Answer: Order 66
  4. The Wrigley Company is spitting distance from the original Goose Island Brewery in what major American city?

    Answer: Chicago
  5. Also known as “The Chairman of the Board,” who sang that Chicago was his “kind of town?”

    Answer: Frank Sinatra
  6. What “M” food conglomerate, based in Chicago, Illinois, owns Cadbury, Chips Ahoy, and Oreo among others? Formerly known as Kraft Foods, it got its name from combining the Latin words for “world” and “delicious.”

    Answer: Mondelez International
  7. If you had professional football tickets to Wrigley Field in the 1930s, you were most likely seeing the Chicago Bears of the Chicago Cardinals, a football team that later decamped for what state?

    Answer: Arizona
  8. Named after a French priest from the 17th century, what Chicago university claims to be the largest Catholic university in the United States?

    Answer: DePaul
  9. The first televised U.S. presidential debate was broadcast from Chicago’s CBS Studios. With one guess, name either of the two men participating in the debate as a presidential candidate.

    Answer: John F Kennedy and Richard Nixon
  10. Founded in Chicago in 1895, what company became the dominant American bicycle manufacturer for much of the 20th century before a 1992 bankruptcy resulted in their sale to Canadian firm Pacific Cycle?

    Answer: Schwinn
  11. Nicknamed “The Bean” for its shape, what is the official name of the giant, shiny steel outdoor sculpture by Anish Kapoor in Chicago’s Millennium Park?

    Answer: Cloud Gate
  12. What management consulting firm, founded in 1926 by a University of Chicago professor, is the biggest of the Big Three management consultancies? In 1975 they debuted overhead value analysis.

    Answer: McKinsey
  13. Covering a variety of topics from manuscript preparation and publication to grammar, usage, and documentation, the widely used “CMOS” stands for “Chicago Manual of” WHAT?

    Answer: Style
  14. Matt Passmore starred as a Chicago police detective who moves to Florida in what early-2010s A&E TV series named after a nickname for a National Park?

    Answer: The Glades
  15. A Chicago bird lover’s society has recently changed its name to the Chicago Bird Alliance, dropping the name of what famous American naturalist due to his support of slavery?

    Answer: Audubon
  16. What store chain was founded in Chicago in 1901, has over eight thousand stores spread across all 50 states, and acquired NYC-based Duane Reade in 2010 for $1 billion?

    Answer: Walgreens
  17. What Chicago-based book was released in 2003 and simultaneously follows dual plot lines of the architecture of the 1893 World’s Fair and the murderous rampage of serial killer Dr. H. H. Holmes?

    Answer: The Devil in the White City
  18. The Amtrak passenger line The City of New Orleans ends in, well, New Orleans. In what Midwestern city does it start?

    Answer: Chicago
  19. Chicago is home to two international airports with flights to over 240 destinations. With one guess, name either of their airport codes.

    Answer: MDW or ORD
  20. In 1983, Chicago elected its first black mayor, a man who shared a surname with another famous “first” politician. Who was this mayor?

    Answer: Harold Washington
  21. The highest-rated daytime talk show in American TV history was a syndicated show that aired for 25 seasons and was filmed in what American city?

    Answer: Chicago (Oprah Winfrey show)
  22. On April 11 2023, it was announced that 2024’s Democratic National Convention would be returning to what U.S. Midwest city that also hosted in 1968 and 1996?

    Answer: Chicago
  23. Michael Hayden’s “Sky’s the Limit” neon art installation can be found lining an underground pedestrian walkway in what Chicago transportation hub?

    Answer: O’Hare Airport
  24. Opening for business in 1893, what hotel located across from Chicago’s Grant Park was declared the most haunted place in Illinois by Travel + Leisure magazine in 2016?

    Answer: Congress Plaza Hotel
  25. What 1970s sitcom, which centered around Chicagoans Florida and James Evans and their family, was spun off from “Maude,” which itself was a spinoff from “All in the Family?”

    Answer: Good Times
  26. Kurt Russell and William Baldwin play Chicago firefighters and brothers who must overcome their differences to solve a string of arson cases in what 1991 film?

    Answer: Backdraft
  27. What “Zen Master” professional sports coach was born in Deer Lodge, Montana? This man later became iconic during coaching stints in Chicago and Los Angeles.

    Answer: Phil Jackson
  28. In 1924, Henry Gerber founded the Society for Human Rights, the first documented gay rights organization in the U.S. In what city was the SHR founded? The organization only lasted a year because of police raids.

    Answer: Chicago
  29. The close results of the 1948 election created the unusual scenario in which Harry Truman won the election, but the Chicago Tribune speculated that what Republican governor of New York was victorious? A celebratory Truman held up this headline while celebrating his win.

    Answer: Thomas Dewey
  30. Ray Kroc’s first McDonald’s opened in 1955 in what Chicago suburb?

    Answer: Des Plaines
  31. According to an urban legend, what type of animal caused the Great Chicago Fire of 1871 by knocking over a lantern?

    Answer: Cow
  32. What famed Chicago-based improv theater group served as a career springboard for Steve Carell, Tina Fey, John Candy, and more?

    Answer: Second City
  33. What expensive restaurant on Walnut Street, Chicago, offers a hand selected New American tasting menu? It shares its name with a member of the blackbird family, and the singular name of a Baltimore sports franchise.

    Answer: Oriole
  34. The band Chicago sings “You’re the meaning in my life” just before singing the title of what hit 1984 song?

    Answer: You’re the Inspiration
  35. What chef won “Top Chef: Chicago,” the show’s fourth season, and is a co-owner of Chi-town restaurants The Girl and the Goat and Little Goat?

    Answer: Stephanie Izard
  36. Michelle Obama was the first director of the Chicago branch of what national movement committed to advancing social justice and equity by engaging and activating the leadership capacities young people? The organization’s two-word name has the initials PA.

    Answer: Public Allies
  37. Morgan Brian is an American athlete that plays for the Chicago Red Stars and also represents the U.S. on the national team. She made her debut in a contest against the Korea Republic in 2013. What sport does Ms. Brian famously play?

    Answer: Soccer
  38. A demonym is a word that identifies a group of people in relation to a particular place, such as Chicagoan or Michigander. What is the official demonym for someone from Austin?

    Answer: Austinite
  39. In “Arsenal of Freedom,” Riker explained that he opted for First Officer duty on the Enterprise instead of captaining what vessel that shares a name with a Chicago hotel and a Canuck rapper?

    Answer: Drake
  40. Founded in Chicago in 1926 by a patent-holder of a mattress design with free-end coils, what is the name of the mattress company that declared bankruptcy in 2009 before being purchased by one of its original owners Edward Bates and revived?

    Answer: Spring Air Company
  41. “Chicago Freestyle” is a 2020 hit song from the album “Dark Lane Demo Tapes” by what one-named rapper who’s more often associated with Toronto than Chicago?

    Answer: Drake
  42. The Chicago Marathon starts in what large urban park that is also nicknamed “Chicago’s Front Yard?”

    Answer: Grant Park
  43. What “S” Aquarium in Chicago’s Museum Campus park opened in 1930 and has a 5 million gallon tank and about 30,000 animals?

    Answer: Shedd Aquarium
  44. What founder of the Women’s International League For Peace and Freedom, which she founded in 1919, who was also a Nobel laureate, is often considered the foundation of social work in the United States? She is often associated with Chicago and Hull House.

    Answer: Jane Addams
  45. The history of indigenous peoples in Canada is explored in the book “A Short History Of Canada”, written by “M” Canadian historian? His last name is the same as a Chicago, IL, US based salt company which features a yellow girl with an umbrella.

    Answer: Desmond Morton
  46. What “B” Fountain is located in the center of Chicago’s Grant Park, and shares its name with the London palace where the Queen lives?

    Answer: Buckingham Fountain
  47. Which American hardware store cooperative that’s based in Chicago is “the place with the helpful hardware folks” not just in the U.S., but in 60 countries worldwide?

    Answer: Ace
  48. A museum dedicated to Jane Addams and the settlement home she founded, Hull House, exists in the Near West Side neighborhood of what large American city?

    Answer: Chicago
  49. Ellen McGrath earned her DVM from the Chicago Veterinary College in 1910. She supposedly holds the incredible distinction as the first woman to practice veterinary medicine. How old was she when she got her veterinarian degree?

    Answer: 22
  50. Born in Chicago in 1901, what was Walt Disney’s middle name?

    Answer: Elias
  51. In what city would you find The Legacy Walk, an outdoor collection of detailed biographical markers celebrating the contributions of LGBTQ+ people to the world? It is the largest collection of such biographical markers in the world.

    Answer: Chicago
  52. What popular Louisville pedestrian bridge gets its name from the former nickname of the Cleveland, Cincinnati, Chicago and St. Louis Railway, which once passed over it?

    Answer: Big Four Bridge
  53. Chicago-based AI company Avant is one of the top contenders for the fastest startup to achieve what magical status, having taken just 1 month and 16 days to hit $1 billion value?

    Answer: Unicorn
  54. In 1912, Walter Burley Griffin from Chicago was announced as the winner of the architectural contest to design which world capital city?

    Answer: Canberra
  55. October 2023 turned out to be a deadly month for birds migrating through what Illinois city after around 1,000 of them crashed into the same building in a single night?

    Answer: Chicago
  56. Which fast food giant has a training facility in Chicago called Hamburger University that has awarded more than 275,000 people with a degree in “Hamurgerology?”

    Answer: McDonald’s
  57. In Season 2 of “Loki” on Disney+, in what city did Mobius and Loki find Victor Timely (a variant of He Who Remains) at the 1893 World’s Fair?

    Answer: Chicago
  58. You could say that what Chicago-based VC firm started by Eric Lefkofsky and Brad Keywell in 2010 illuminates promising startups (like Groupon and Udemy)?

    Answer: Lightbank
  59. What fictional puppet goose, namesake of a children’s television show that ran on Chicago television in the late 1950s and early 1960s, proclaimed himself to be “King of the United States”?

    Answer: Garfield Goose
  60. The International Museum of Surgical Science in Chicago serves as a macabre dedication to the art of cutting people open, including a surgeon “Hall of Fame.” Included in the museum’s archives are letters and journals from what famous English statistician who is often considered the founder of modern nursing?

    Answer: Florence Nightingale

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Wednesday Trivia Chicago

  1. What day is the Chicago Riverwalk officially closed for cleaning? (Answer: Wednesday)

2. Which iconic Chicago landmark features a “hump day” sculpture?

(Answer: Cloud Gate, aka “The Bean”)

3. What popular Chicago pizza chain offers a “Wacky Wednesday” deal?

(Answer: Lou Malnati’s)

4. Which Chicago museum hosts free “Wellness Wednesdays” with yoga and meditation?

(Answer: The Art Institute of Chicago)

5. What historic Chicago theater offers discounted “Wednesday Matinees”?

(Answer: The Goodman Theatre)

6. Which beloved Chicago park hosts a “Woof Wednesday” dog playgroup?

(Answer: Lincoln Park)

7. What local brewery hosts “Mug Club Wednesdays” with exclusive discounts?

(Answer: Goose Island Brewery)

8. What iconic Chicago hot dog stand offers a “Hump Day Special”?

(Answer: Portillo’s)

9. Which Chicago comedy club features “Wednesdays are Wild” open mic nights?

(Answer: Second City)

10. What popular Chicago coffee shop hosts “Writer Wednesdays” with open writing sessions?

(Answer: The Book Cellar)

11. What historic event in Chicago history happened on a Wednesday?

(Answer: The Great Chicago Fire of 1871)

12. Which Chicago sports team traditionally plays their home games on Wednesdays?

(Answer: The Chicago Blackhawks)

13. What popular Chicago festival takes place every Wednesday in the summer?

(Answer: Navy Pier’s “Chicago Wednesdays”)

14. Which Chicago musician released a hit song titled “Chicago Wednesday”?

(Answer: The Lawrence Arms)

15. What iconic Chicago landmark was officially dedicated on a Wednesday?

(Answer: Millennium Park)

16. Which Chicago neighborhood holds a “Whiskey Wednesdays” bar crawl event?

(Answer: Wicker Park)

17. What local Chicago radio station features a “Wacky Wednesday” morning show segment?

(Answer: 101.9 The Mix)

18. Which Chicago art gallery hosts “Wine and Whine Wednesdays” with art discussions and refreshments?

(Answer: The Zhou B Art Center)

19. What local Chicago gym offers “Workout Wednesdays” with free fitness classes?

(Answer: The Sweat Cycle)

20. Which Chicago bookstore hosts “Author Wednesdays” with book readings and signings?

(Answer: The Book Loft

21. What lesser-known nickname is associated with Chicago Wednesdays?

(Answer: “Hump Day Headquarters”)

22. Which Chicago-based artist created a series of paintings titled “Chicago Wednesdays”?

(Answer: Kerry James Marshall)

23. What quirky Chicago tradition takes place every Wednesday at noon?

(Answer: The Buckingham Fountain dolphin show)

24. Which Chicago restaurant offers a “Secret Wednesday” menu with hidden dishes?

(Answer: Roister)

25. What hidden gem park in Chicago hosts a “Nature Wednesdays” program with guided walks? (Answer: North Park Village Nature Center)

26. Which Chicago brewery releases a limited-edition beer only on Wednesdays?

(Answer: Half Acre Beer Company)

27. What vintage clothing store in Chicago hosts a “Wednesdays in the Wardrobe” fashion show? (Answer: Penelope’s)

28. Which Chicago museum offers extended hours and free admission on Wednesdays?

(Answer: The Museum of Contemporary Art Chicago)

29. What secret speakeasy in Chicago is only open on Wednesdays?

(Answer: The Aviary)

30. What hidden message or symbol can be found on a Chicago landmark on Wednesdays?

(Bonus points for identifying the landmark and message!)

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Old Chicago Trivia Night

  1. What year did the first Old Chicago open its doors? (Answer: 1975)

2. Which city holds the claim to the original Old Chicago location?

(Answer: Chicago, Illinois)

3. What was the inspiration behind the brewery’s name?

(Answer: The Great Chicago Fire of 1871)

4. What iconic Chicago landmark is featured in the Old Chicago logo?

(Answer: The Water Tower)

5. What is the official mascot of Old Chicago?

(Answer: The Old Chicago Brewer)

6. Old Chicago is known for its extensive selection of what type of beer?

(Answer: Craft beers)

7. Which Old Chicago beer is brewed with hops grown right on the rooftop of some locations?

(Answer: Hop Project)

8. What is the name of Old Chicago’s seasonal pumpkin beer?

(Answer: Pumpkinhead)

9. Besides beer, what other beverage is a popular choice at Old Chicago?

(Answer: Old Chicago Root Beer)

10. What is the signature appetizer dish often served with beer at Old Chicago?

(Answer: Beer Cheese & Pretzels)

11. What hidden message can be found on the bottom of some Old Chicago beer glasses?

(Answer: “Drink Responsibly”)

12. Which famous musician or band has performed at an Old Chicago location?

(Bonus points for naming the city!)

13. What is the name of the Old Chicago loyalty program?

(Answer: Brew Crew Club)

14. What unique event does Old Chicago host annually that features limited-edition beers?

(Answer: World Beer Cup Week)

15. What is the “secret ingredient” in the Old Chicago chili recipe?

(Answer: Coffee)

16. How many states does Old Chicago currently have locations in?

(Bonus points for the exact number!)

17. What is the name of Old Chicago’s philanthropic initiative that supports local communities?

(Answer: Old Chicago Hops for Hope)

18. What is the largest Old Chicago location by square footage?

(Bonus points for the city!)

19. What lesser-known food item is surprisingly popular at Old Chicago?

(Answer: Fried pickles)

20. Can you name a celebrity who is known to be a fan of Old Chicago beer?

(Bonus points for the celebrity!)

University of Chicago Trivia Questions and Answers

  1. What nickname do UChicago students and alumni proudly wear? (Answer: Maroons)

2. In what year did the University of Chicago open its doors to knowledge seekers?

(Answer: 1890)

3. What Latin motto encapsulates UChicago’s dedication to learning and growth?

(Answer: “Let knowledge grow from more to more”)

4. Which iconic Gothic structure stands sentinel on the UChicago campus?

(Answer: Rockefeller Memorial Chapel)

5. What beloved green spaces connect the academic buildings, forming the heart of campus life?

(Answer: The Quads)

6. UChicago boasts an impressive number of Nobel laureates. Can you guess how many?

(Answer: 99, as of 2023)

7. What unique academic division fosters interdisciplinary exploration at UChicago?

(Answer: The College)

8. Though not as cuddly as a real bear, who represents the Maroon spirit?

(Answer: Maroon the bear, the official mascot)

9. What classic color combination proudly adorns UChicago merchandise and school spirit?

(Answer: Maroon and gold)

10. When the Maroons raise their voices, what traditional song fills the air?

(Answer: “Alma Mater” or “Chicago”)

11. Shrouded in secrecy and known for playful pranks and hidden philanthropy, what UChicago society stirs curiosity?

(Answer: The Order of the C)

12. Can you navigate the hidden Hogwarts-inspired staircase rumored to exist on campus?

(Answer: The Hutchinson Commons staircase)

13. Keeping watch over the Divinity School, what gargoyle earns the nickname “The Eye of God”?

(Answer: The Divinity School gargoyle)

14. What annual student tradition sends Maroons on a citywide quest for clues and hidden treasures? (Answer: The Scavenger Hunt)

15. As the academic year draws to a close, what vibrant celebration marks the end of an era for graduating Maroons?

(Answer: Mayfest)

16. From Saul Bellow to Toni Morrison, UChicago has nurtured some of the greatest literary minds. Can you name two other famous UChicago alumni in the world of literature?

(Open-ended bonus question)

17. The field of economics owes much to UChicago’s intellectual giants. Can you name two Nobel laureates in economics affiliated with UChicago besides Milton Friedman?

(Gary Becker, Ronald Coase, Robert Fogel, Milton Friedman, Merton Miller, Theodore Schultz and George Stigler)

18. Science, too, has benefitted from UChicago’s brilliance. Can you name two prominent scientists who have ties to the university?

(Crick, Franklin, Watson, and Wilkins)

19. UChicago alumni have made their mark on politics and activism as well. Can you name two notable figures besides Michelle Obama, Hillary Clinton, and Bernie Sanders?

(Open-ended bonus question)

20. Beyond the academic realm, UChicago has even graced the silver screen. Can you recall the movie that featured the university and its unique campus culture?

(Answer: “The Perks of Being a Wallflower”)

Read Also: 250+ Best Mario Trivia Questions and Answers (Easiest to Hardest)

Chicago Trivia Facts

  1. The Windy City (though the wind isn’t actually stronger than other cities!)
  2.  Cloud Gate (“The Bean”) in Millennium Park
  3. State Street marks the north-south division of the city.
  4.  Chicago Riverwalk Kayak Marathon takes place annually.
  5. Willis Tower (formerly Sears Tower) once held the title of tallest building in the world.
  6. Deep-dish pizza reigns supreme in Chicago.
  7. Vienna Beef hot dogs boast the slogan “No ketchup, no mustard, just relish.”
  8. Wicker Park is known for its vibrant jazz scene.
  9. Muddy Waters is a legendary Chicago blues musician.
  10. The University of Chicago is nicknamed the Maroons.
  11. The Onion Patch
  12. The Great Chicago Fire of 1871 reshaped the city’s landscape.
  13.  Tiltworld features upside-down houses and a tilted fountain.
  14. John Dillinger was a notorious gangster from Chicago.
  15. The Loop houses Broadway-caliber productions.
  16. Lincoln Park 2550 offers a stunning view of the city skyline.
  17. The Art Institute of Chicago was designed by Shepley, Rutan and Coolidge.
  18. The Art Institute’s Thorne Miniature Rooms showcase miniature replicas of world landmarks.
  19. Ramona Quimby’s adventures take place in Chicago.
  20. The Blue Chicago is a legendary blues club that hosted Muddy Waters and B.B. King.
  21. The Gateway to Freedom
  22. The Tribune Tower held the title of tallest building for a time.
  23. The Pedway connects buildings in the Loop underground.
  24. H.H. Holmes terrorized Chicago.
  25. Terracotta terracing adorns the Wrigley Building.
  26. WVON played a crucial role in pioneering blues broadcasting.
  27. North Park Village Nature Center boasts a sanctuary and working farm.
  28.  Edward Buckingham designed the iconic Buckingham Fountain.
  29. Frank Lloyd Wright designed the iconic Chicago bungalow style.
  30. The Chicago St. Patrick’s Day Parade is a beloved annual event.

Frequently Asked Questions

How long is Trivia Joe’s on Weed Chicago?

Joe’s on Weed St. is open from 5:00 PM to 2:00 AM on Fridays and Saturdays, and from 10:30 AM to 2:00 AM on Saturdays

Is beer money sports trivia Chicago on wow cable TV?

Beer Money Sports Trivia Chicago is not currently airing on Wow Cable TV.

What is the motto of Chicago?

Chicago’s motto is urbs in horto or “city in a garden.” 


Chicago Trivia questions test your knowledge of the wind city. Get acquainted with this list of best Chicago trivia, learn the answers, and go play at any bar in Chicago.

So, form a team and practice these trivia questions before heading to the Chicago trivia host this Wednesday.