156 Chicago Trivia Questions (Ranked from Easiest to Hardest)

Chicago, also known as the "Windy City," is the third-largest city in the United States and the largest city in the state of Illinois. The city is known for its rich history, culture, and landmarks such as Willis Tower (formerly known as the Sears Tower) and Wrigley Field.

Chicago was founded in 1833 by a group of settlers led by John Kinzie and was incorporated as a city in 1837. The city quickly grew in the late 19th and early 20th centuries, becoming a major transportation hub and center of industry. This growth led to the development of many famous neighborhoods and landmarks, including the Willis Tower and Wrigley Field.

Chicago is also known for its diverse population and cultural influences, with a large number of immigrants from Ireland, Poland, and Italy, as well as African American and Hispanic communities. This diversity is reflected in the city's food, music, and art, making it a vibrant and exciting place to visit or live.

156 Chicago Trivia Questions Ranked From Easiest to Hardest (Updated for 2025)

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 exploded in popularity across the U.S. 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 called 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. In 1996, the Democratic National Convention returned to Chicago after a 28 year break. A professional championship also returned to the city that year, but after a much shorter hiatus. Which hoop team won a title in 1996 to go along with their rings in ‘91, ‘92, ‘93, ‘97, and ‘98?

Answer: Chicago Bulls

7. Named after the inventor George who first constructed it at the 1893 Chicago World’s Fair, what carnival attraction could refer to the London Eye, the Singapore Flyer, or the Ain Dubai?

Answer: Ferris Wheel

8. 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

9. If you vist 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. It was also the location where which media titan filmed her titular show behind the famous Harpo Studios banner?

Answer: Oprah Winfrey

10. 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

11. 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

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

Answer: American Automobile Association

13. 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

14. Alan Ruck makes his way to the city as Cameron Frye in what 1986 film filled with Chicago landmarks like Wrigley Field, the Art Institute, and the Sears Tower?

Answer: Ferris Bueller's Day Off

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

Answer: Dreamgirls

16. 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

17. 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

18. In 1962, what U.S. city took inspiration from pollution-control workers and dyed its namesake river green to celebrate St. Patrick's Day?

Answer: Chicago

19. If you walked due east from the tip of Navy Pier, you'd walk into a lake. If you could walk on water and continue east, what would be your first step on land in what U.S. state?

Answer: Michigan

20. What is the feline name of the sports teams of Northwestern University?

Answer: Wildcats

21. Initially launched in 2013 with 750 bikes and 75 docking stations, what is the name of Chicago's bike-share system?

Answer: Divvy

22. What orthopedics brand with a blue-and-white logo was founded in 1906 by a Chicago shoemaker's apprentice while he was in medical school at the time?

Answer: Dr. Scholl's

23. Which of the eight lines on Chicago's famed "L" system served the most passengers in 2018?

Answer: Red Line

24. What American director adapted the ancient Greek drama "Lysistrata" to the modern-day South Side in the 2015 film "Chi-Raq?"

Answer: Spike Lee

25. 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

26. What park and conservatory on Central Park Avenue in Chicago shares its name with the 20th U.S. president, as well as a famous Jim Davis creation?

Answer: Garfield Park Conservatory

27. Anish Kapoor's public sculpture "Cloud Gate," installed in Chicago's Millennium Park, is better known by what legume-y nickname?

Answer: The Bean

28. 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

29. 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

30. 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

31. What triple-A minor league baseball affiliate of the Chicago White Sox plays its home games at Truist Field in Charlotte, North Carolina?

Answer: Charlotte Knights

32. The 1892 convention nominates Adlai Stevenson I for veep. Chicago commuters are likely more familiar with his grandson, Interstate 55 namesake Adlai Stevenson II. Another major Chicago expressway, I-290, is named after what like-able president that defeated Stevenson II in 1952 and 1956 and signed off on the interstate system?

Answer: Dwight D. Eisenhower

33. Which of the Chicago "L" system's colored lines has the fewest stations at three: Howard, Oakton-Skokie, and Dempster-Skokie?

Answer: Yellow

34. 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

35. 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

36. 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

37. Measured by the number of students, what is the largest college in the state with the word “Chicago” in its full name?

Answer: University of Illinois at Chicago

38. North Michigan Avenue in Chicago is home to what “central” 100-floor skyscraper? It’s funded by a life insurance company that got its name from a president of the Continental Progress with an alleged big signature.

Answer: John Hancock Center

39. 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

40. 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 is his other half?

Answer: Keegan-Michael Key

41. Because of its oblong shape, Chicago's giant metal "Cloud Gate" sculpture is nicknamed for what staple food?

Answer: Bean

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

Answer: Intelligentsia

43. 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

44. 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

45. Which American sitcom that ran on CBS from 1972-1978 featured a famous comedian (with his name in the title, like Mary Tyler Moore’s) as a psychologist named Robert Hartley living in Chicago with his wife Emily?

Answer: The Bob Newhart Show

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

Answer: Baseball

47. While it was nominated for five Oscars after its 1970 release, not everyone enjoyed "Tora! Tora! Tora!" What Chicago Sun-Times film critic, Siskel’s long-time partner, gave it one star and called it "one of the deadest, dullest blockbusters ever made”?

Answer: Roger Ebert

48. 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

49. The Wrigley Company is spitting distance from the original Goose Island Brewery in what major American city?

Answer: Chicago

50. Also known as "The Chairman of the Board," who sang that Chicago was his "kind of town?"

Answer: Frank Sinatra

51. With the Republican and Democratic conventions both in Chicago in 1944, there were plenty of mouths to feed. Ike Sewell and Richard Riccardo picked an opportune time to invent deep dish at what pizzeria that shares its apt numerical name with a certain card game?

Answer: Pizzeria Uno

52. What “M” food conglomerate based in Chicago 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

53. 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

54. The first televised U.S. presidential debate was broadcast from Chicago's CBS Studios. Name the two men participating in the debate as presidential candidates.

Answer: John F Kennedy and Richard Nixon

55. 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

56. 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

57. 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

58. In a famous scene from 1986's "Ferris Bueller's Day Off," Ferris and co. snag a table at the snooty restaurant Chez Quis by impersonating Abe Froman, the WHAT King of Chicago?

Answer: Sausage

59. 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

60. What store chain was founded in Chicago in 1901, has over 8,000 stores spread across all 50 states? It acquired NYC-based Duane Reade in 2010 for $1 billion.

Answer: Walgreens

61. 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

62. 1868 was a big year for New Yorkers in Chicago. Schuyler Colfax earned the vice presidential nomination, and two swans from Central Park were the first animals at Chicago’s Lincoln Park Zoo. The zoo, which attracts 3 million visitors a year, has an agreement until 2049 to keep its admission at what very affordable rate?

Answer: Free

63. The Amtrak passenger line The City of New Orleans ends in, well, New Orleans. In what Midwestern city does it start?

Answer: Chicago

64. Chicago is home to two international airports with flights to over 240 destinations. What are the airport codes?

Answer: MDW/ORD

65. In 1983, Chicago elected its first Black mayor, a man who shared a surname with another famous "first" politician. Who was he?

Answer: Harold Washington

66. The highest-rated daytime talk show in American TV history was a syndicated show that aired for 25 seasons—The Oprah Winfrey Show. It was filmed in what American city?

Answer: Chicago

67. 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

68. 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

69. 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

70. In 2024, one U.S. city’s most expensive property, a 25,000-square-foot mansion in Lincoln Park, sold for $15.25 million. It sounds like a lot, but the sale actually had a ~$50 million loss if you factor in the price when it was first listed back in 2016. What city was the residence in?

Answer: Chicago

71. 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

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

Answer: Chicago

73. Think of the word that means "a small, pond-like body of water that is often connected to a larger body of water." Now translate that word into Spanish and use the diminutive form. What American beer brand from Chicago do you have?

Answer: Lagunitas

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

Answer: Second City

75. What expensive restaurant on Walnut Street in 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

76. According to an urban legend, what type of animal caused the Great Chicago Fire of 1871 by knocking over a lantern?

Answer: Cow

77. 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

78. 1960 was the most recent year the Republican National Convention was held in Chicago. If attendees wanted to enjoy a laugh while in town, they could hit up what new improv troupe that eventually produced Bill Murray, John Belushi, Amy Poehler, Tina Fey, and Cecily Strong?

Answer: The Second City

79. 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

80. 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 she famously play?

Answer: Soccer

81. Founded in Chicago in 1926 by a patent-holder of a mattress design with free-end coils, what mattress company declared bankruptcy in 2009 before being purchased by one of its original owners, Edward Bates, and revived?

Answer: Spring Air Company

82. The Chicago Marathon starts in what large urban park that is also nicknamed "Chicago's Front Yard?"

Answer: Grant Park

83. 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

84. What founder of the Women’s International League For Peace and Freedom was also a Nobel laureate and is often considered the foundation of social work in the United States? She is often associated with Chicago and Hull House.

Answer: Jane Addams

85. 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

86. 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

87. 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

88. 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

89. Born in Chicago in 1901, what was Walt Disney’s middle name?

Answer: Elias

90. 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

91. 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

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

Answer: Unicorn

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

Answer: Canberra

94. 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

95. 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

96. The oldest still-operating real estate brokerage firm in the United States was started in Chicago in 1855 and called L.D. Olmsted & Co.” Today, it’s known as Baird & WHO?

Answer: Warner

97. 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

98. 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

99. Headquartered in Chicago, what is the largest Law firm in the U.S. in terms of employed attorneys, with a recent count of 4720 lawyers working for them?

Answer: Baker McKenzie

100. Michael Jordan came out of retirement to play for two seasons in the 1990s with the Washington Wizards, having played all his previous NBA seasons with what Eastern Conference team?

Answer: Chicago Bulls

101. The South Side cocktail, made from gin, lime juice, simple syrup, and mint, may have been named for the South Side of Chicago, where it was a favorite of what local and notorious bootlegger?

Answer: Al Capone

102. 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." 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

103. The Big Five U.S. accounting firms became the Big Four after the 2002 dissolution of what alliterative, Chicago-based firm?

Answer: Arthur Andersen

104. Considered a modern classic, what alliterative bourbon-Aperol cocktail was invented in 2007 in Chicago and named after a hit M.I.A. song?

Answer: Paper Plane

105. "Nuclear Energy" is a bronze sculpture by Henry Moore located on the campus of what school? The sculpture marks the location of the world's first nuclear reactor, Chicago Pile-1.

Answer: University of Chicago

106. What Midwestern school is often associated with the "dismal science" of Economics in part due to boasting over two dozen Nobel Prize winners in the field?

Answer: University of Chicago

107. "A Midsummer Night's Dream" inspired the French film "L'Appartement," which was remade into a 2004 Josh Hartnett movie named for what Chicago neighborhood?

Answer: Wicker Park

108. Headquartered in Chicago, what "H" hospitality corporation owns brands including Miraval resorts as well as the Andaz and Caption hotel lines?

Answer: Hyatt

109. U.S. Route 66 also known as the Main Street of America or the Mother Road, was one of the original highways in the U.S. Highway System and was established in 1926 with a starting place in what major American city?

Answer: Chicago

110. The history of Chicago's Windy City nickname is dotted with controversy, but the first repeated effort to label Chicago with this monker comes from an 1870s rivalry with what other Midwestern city that also starts with a "C?"

Answer: Cincinnati

111. Hungarian-born British conductor Georg Solti has the record for most Grammy Awards, with a whopping 31 wins. He won as conductor of the orchestra for what Midwestern U.S. city?

Answer: Chicago

112. In 2019, pair of rare Piping Plovers named Monty and Rose (after their nesting site of Montrose Beach) became famous as the first nesting pair to appear in what U.S. city in decades?

Answer: Chicago

113. All in the Family led to the spin-off "Maude,” which in turn led to what "Dy-no-mite" spin-off from the 1970s set in a Chicago housing project?

Answer: Good Times

114. After Chicago, what is the most populous U.S. city in the Central Time Zone? Hint: These places are about 1,000 miles apart from each other.

Answer: Houston

115. Although the Big 10 Conference has gained many schools over the years, only one has left it. What is the school, which is often considered the most prestigious university in the state of Illinois?

Answer: University of Chicago

116. The Cincinnati Reds won the 1919 World Series five games to three over what opposing team, a victory tainted by the scandalous revelation that this opponent had conspired to throw the series?

Answer: Chicago White Sox

117. 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

118. What African-American lawyer founded The Chicago Defender in 1905, one of the most successful black-owned newspapers in the U.S.? His last name is the same as that of Lou Costello’s comedy partner.

Answer: Robert Abbott

119. A major Chicago establishment, the Greater North Michigan Avenue Association owns what alliterative trademark that describes the extravagance and the length of a particular section of Chicago commerce?

Answer: Magnificent Mile

120. What head coach helped the Chicago Cubs snap its 108-year championship drought by winning the 2016 World Series with a Game 7 victory over the Cleveland Indians?

Answer: Joe Maddon

121. A number of real historical Chicago locations appear in what 1987 Brian de Palma film that stars Kevin Costner as Eliot Ness?

Answer: The Untouchables

122. While Gloria Jean Kvetko founded her coffee brand in 1970s Chicago, what down-under city is the company’s headquarters in today, thanks to a franchising sale in the ‘90s?

Answer: Sydney

123. What chocolate treat produced by Hershey got its name because the creators, Hoffman and Company of Chicago, were unable to achieve their desired spherical shape?

Answer: Milk Duds

124. Unsurprisingly, this Chicago neighborhood take its name from a local park, and the park's name is derived from a 19th-century alderman who helped establish the park in the "Polish Gold Coast" area of the city. What is this neighborhood?

Answer: Wicker Park

125. What two Chicago streets intersected to form an area known for many years as "the world's busiest corner?"

Answer: State and Madison

126. Lorem ipsum text comes from a 1st century BCE speech by what Roman statesman and namesake of a Chicago-area town?

Answer: Cicero

127. What is the name of the richest "city" (technically a "village" with a population of ~9,000) in the Chicago area? It’s #10 on the overall U.S. cities list, with an average income of $340,000, and surrounded by three other high income communities: Highland Park, Northbrook, and Winnetka.

Answer: Glencoe

128. The headquarters for Motorola Mobility, Conagra, and Jim Beam Suntory are all located at what Chicago location, which was the largest building in the world from 1931 to 1943?

Answer: Merchandise Mart

129. Roger Ebert became the first film critic to win a Pulitzer for Criticism while thumbing movies for what Windy City daily?

Answer: Chicago Sun-Times

130. In 1893, Ida B. Wells joined Frederick Douglass and other Black leaders for a boycott of the World's Columbian Exposition in what Midwest city?

Answer: Chicago

131. "Dewey Defeats Truman" was a headline that should not have been printed, as incumbent U.S. President Harry Truman defeated Governor Thomas Dewey of New York in the 1948 Presidential election. Which major-city newspaper ran this headline on November 3, 1948 and almost immediately regretted it?

Answer: Chicago Tribune

132. What German candy company known for its square chocolate bars opened a U.S. subsidiary headquartered in Chicago in 2024?

Answer: Ritter Sport

133. The Inter-Ocean was a popular newspaper from from the end of the Civil War until 1914. This somewhat unusual name for the paper made more sense when one realized that what large American city was home to the paper's headquarters?

Answer: Chicago

134. Lonnie Rashid Lynn, Jr was born in Chicago's Hyde Park neighborhood to a former professional basketball player and educator. After almost a dozen years in the music industry, he earned his first (of many) acting credits in 2003, appearing on the the sitcom "Girlfriends." What one-word moniker is he better known by?

Answer: Common

135. The Devil Baby of Hull House is a Chicago urban legend that is said to have inspired what 1967 Ira Levin horror novel and its film adaptation?

Answer: Rosemary's Baby

136. The longest MLB game in history in terms of time played was a 25-inning game between the Chicago White Sox and the Milwaukee Brewers in 1984. It took just over eight hours and took place at which two-word Chicago stadium?

Answer: Comiskey Park

137. The 1909 Plan of Chicago recommended new and widened streets, parks, new railroad and harbor facilities, civic buildings, and much more. The document had a massive influence on the field of city planning. One of the co-authors lent his name to the Plan. What was his surname?

Answer: Burnham

138. What psychology professor at the University of Chicago and Harvard came up with six stages of moral development that a person goes through? His states include morality for personality benefit, morality conforming to social norms, and finally, morality that best works for everyone.

Answer: Lawrence Kohlberg

139. Bigger Thomas, a young Black man living in poverty in Chicago in the 1930s, is the title character of what novel by Richard Wright?

Answer: Native Son

140. A traditional "Chicago handshake" is a shot-and-a-beer combo that pairs Heileman's Old Style with what noxious Jeppson's liqueur?

Answer: Malört

141. Featuring four rows of keys, the Chicago Theatre's massive organ was made by what "W" company from Germany?

Answer: Wurlitzer

142. In 1994, during his hiatus from the NBA, Michael Jordan played one season of baseball with what double-A minor-league affiliate of the Chicago White Sox?

Answer: Birmingham Barons

143. What eponymous cosmetics brand was founded by a woman born in Chicago who graduated from college with a self-directed degree in theatrical makeup? In 1991, she and her husband partnered with another couple to launch a brand that debuted at Bergdorf Goodman in New York City.

Answer: Bobbi Brown

144. If you had a ticket to the World's Fair (the Columbian Exposition) in 1893, you'd be visiting what American city?

Answer: Chicago

145. The building regarded as the world’s first skyscraper, the Home Insurance building, was built in 1884 in which American city?

Answer: Chicago

146. What was the first name of the half of the legendary rock and roll duo The Everly Brothers, who was born in Brownie, Kentucky in 1937, two years before his brother Phil was born in Chicago?

Answer: Don

147. Deemed the second best podcast of 2020 by The Atlantic, what true crime podcast follows Shapearl Wells as she investigates the 2016 murder of her son in Chicago?

Answer: Somebody

148. The Chicago Blackhawks won the Stanley Cup in 2015, defeating what Eastern Conference team in the finals?

Answer: Tampa Bay Lightning

149. What Latina and Chicago native wrote "Caramelo," a novel about a Mexican-American family in Chicago who takes an annual road trip to visit their “Awful Grandmother” in Mexico City?

Answer: Sandra Cisneros

150. Which startup founded in Chicago in 2017 boasts its services as the “purrfect” way for developers to manage in-app purchases and subscriptions?

Answer: RevenueCat

151. The American _______ Association (AHA) is a healthcare industry trade group headquartered in Chicago that’s been around for almost 125 years. Today, the network of providers in the United States, many of who partake in its professional membership groups, is close to 5,000.

Answer: Hospital

152. Nicknamed "Commy" or "the Old Roman," what Chicago native helped form the American League, owned one of its teams, and was inducted into the Baseball Hall of Fame in 1939?

Answer: Charles Comiskey

153. At the intersection of Richards Drive and Hayes Drive in Jackson Park lies a sculpture somewhat generically named and created as a celebration of the Columbian Exposition's 25th anniversary. What is the name of this Daniel Chest French statue?

Answer: Statue of the Republic

154. Which of August Wilson's ten "Pittsburgh Cycle" plays is the only one not actually set in Pittsburgh? Set in a Chicago recording studio, it was made into an Oscar-nominated film in 2020.

Answer: Ma Rainey's Black Bottom

155. The 1909 Plan of Chicago recommended an entire network of new diagonal streets, but only one was ever built. What is the name of this avenue?

Answer: Ogden Avenue

156. Despite its name, which Chicago-based insurance company isn’t just for financiers?

Answer: Bankers Life

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