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.
176 Chicago Trivia Questions Ranked From Easiest to Hardest (Updated for 2024)
- 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
- 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
- The Chicago skyscraper still informally known by its original name, the Sears Tower, has been officially named what since 2009?
Answer: The Willis Tower
- 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
- 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
- At what baseball stadium is Ferris Bueller spotted during his titular romp though a "sick day" in the streets of Chicago?
Answer: Wrigley Field
- 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
- 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
- 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
- Let’s look backwards! 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 - 2014, that was the same location that what media titan filmed her titular show behind the famous Harpo Studios banner?
Answer: Oprah Winfrey Show
- 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
- 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
- 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
- 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
- Chicago native Jennifer Hudson won both an Oscar and a Golden Globe for her performance in what 2006 musical film?
Answer: Dreamgirls
- 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
- 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
- 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
- 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
- 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
- Rowr! What is the feline name of the sports teams of Northwestern University?
Answer: Wildcats
- Initially launched in 2013 with 750 bikes and 75 docking stations, what is the name of Chicago's bike-share system?
Answer: Divvy
- 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
- Which of the 8 lines on Chicago's famed "L" system served the most passengers in 2018?
Answer: Red Line
- 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
- What American director adapted the ancient Greek drama "Lysistrata" to the modern-day South Side in the 2015 film "Chi-Raq?"
Answer: Spike Lee
- 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
- 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
- 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
- Anish Kapoor's public sculpture "Cloud Gate," installed in Chicago's Millennium Park, is better known by what legume-y nickname?
Answer: The Bean
- 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
- 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
- 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
- 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
- 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
- What is the trademarked term that describes a section of Michigan Avenue running from the Chicago River to Oak Street?
Answer: The Magnificent Mile
- Which of the Chicago "L" system's colored lines has the fewest stations, with just three: Howard, Oakton-Skokie, and Dempster-Skokie?
Answer: Yellow
- 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
- 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
- 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
- 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
- Chicagoan Gwendolyn Brooks became the first African-American woman to win what literary prize in 1949?
Answer: Pulitzer Prize
- 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
- Because of its oblong shape, Chicago's giant metal "Cloud Gate" sculpture is nicknamed for what staple food?
Answer: Bean
- What Chicago-based coffee brand has a 14-letter name that means the highly educated members of a society as a group?
Answer: Intelligentsia
- 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
- 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
- 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
- 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
- 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
- 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
- Mostly seen on a certain Chicago dish, sport peppers most likely got their name from being served during games of which sport?
Answer: Baseball
- 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
- The Wrigley Company is spitting distance from the original Goose Island Brewery in what major American city?
Answer: Chicago
- Also known as "The Chairman of the Board," who sang that Chicago was his "kind of town?"
Answer: Frank Sinatra
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- The Amtrak passenger line The City of New Orleans ends in, well, New Orleans. In what Midwestern city does it start?
Answer: Chicago
- 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
- 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
- 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)
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Ray Kroc’s first McDonald’s opened in 1955 in what Chicago suburb?
Answer: Des Plaines
- According to an urban legend, what type of animal caused the Great Chicago Fire of 1871 by knocking over a lantern?
Answer: Cow
- What famed Chicago-based improv theater group served as a career springboard for Steve Carell, Tina Fey, John Candy, and more?
Answer: Second City
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- "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
- The Chicago Marathon starts in what large urban park that is also nicknamed "Chicago's Front Yard?"
Answer: Grant Park
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Born in Chicago in 1901, what was Walt Disney’s middle name?
Answer: Elias
- 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
- 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
- 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
- In 1912, Walter Burley Griffin from Chicago was announced as the winner of the architectural contest to design which world capital city?
Answer: Canberra
- 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
- 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
- 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
- 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
- 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
- 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
- The Big Five U.S. accounting firms became the Big Four after the 2002 dissolution of what alliterative, Chicago-based concern?
Answer: Arthur Andersen
- The lead singer says of the titular day, "I think it was the Fourth of July," in what 1972 number-three hit song by Chicago?
Answer: Saturday in the Park
- "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
- "Jesus Just Left Chicago" is a track from the 1973 album "Tres Hombres" by what American rock band that comes at the end of the alphabet?
Answer: ZZ Top
- 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
- "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
- What Chicago landmark was built in 1869, is the 2nd oldest of its kind in the nation, and was described by Oscar Wilde as "a castellated monstrosity with pepper boxes stuck all over it"?
Answer: Water Tower
- Headquartered in Chicago, what "H" hospitality corporation owns brands including Miraval resorts as well as the Andaz and Caption hotel lines?
Answer: Hyatt
- The Chicago Board of Trade shut down in 1906 to honor the death of what local retail titan? His namesake chain was later acquired by Macy's.
Answer: Marshall Field
- 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
- The history of Chicago's Windy City nickname is dotted with controversy, but the first repeated effort to label Chicago with this nickname comes from an 1870s rivalry with what other Midwestern city that starts with a C?
Answer: Cincinnati
- Hungarian-born British conductor Georg Solti has the record for most Grammy Awards, with a whopping 31 wins. He won these awards as the conductor of the Orchestra for what midwestern US city?
Answer: Chicago
- Headquartered in Colorado, what repetitively named company claims to be the world's leading provider of in-flight Internet and entertainment?
Answer: Gogo
- What Illinois public university has a mascot that commemorates a historic 1871 event?
Answer: UIC Flames
- What word that could also be used to describe a certain MLB or NFL player is the name of a long-distance Amtrak passenger line that stops at Cincinnati en route from New York to Chicago?
Answer: Cardinal
- 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
- Although the Big 10 Conference has gained many schools over the years, only one school has left the conference. What is this school that is often considered the most prestigious university in the state of Illinois?
Answer: University of Chicago
- 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
- What Chicago-based restaurant chain was founded in 1963 as "The Dog House" and featured Chicago-style foods such as hot dogs, Maxwell Street Polish, and Italian Beef?
Answer: Portillos
- After Chicago, what is the most populous U.S. city in the Central Time Zone? Hint: They're about 1,000 miles apart from each other.
Answer: Houston
- The modern NBA team known as the Washington Wizards began their journey in Chicago as the Packers. Before finally landing in Washington, D.C., the team was transferred to what charming city of the Eastern US?
Answer: Baltimore
- What African-American lawyer founded The Chicago Defender in 1905, one of the most successful black-owned newspapers in the US? His last name is the same as the last name of Lou Costello’s comedy partner.
Answer: Robert Abbott
- 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
- A number of real historical Chicago locations appear in what 1987 Brian de Palma film, which stars Kevin Costner as Eliot Ness?
Answer: The Untouchables
- What Canadian crime comedy-drama aired from 1994 to 1999 and starred Paul Gross as a Royal Canadian Mounted Police (RCMP) officer who has a deaf wolf as a pet and helps the Chicago police department?
Answer: Due South
- On 31 May 1942, Japanese submarines fired upon the USS Chicago and hit one of the local ferries in the harbor of which Southern Hemisphere City?
Answer: Sydney
- What chocolate treats made currently produced by Hershey gets its name because its creators, Hoffman and Company of Chicago, were unable to achieve their desired spherical shape?
Answer: Milk Duds
- 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
- What two Chicago streets intersected to form an area known for many years as "the world's busiest corner?"
Answer: State and Madison
- What department store had the mottoes "As Chicago as it gets" and "Give the lady what she wants" at different points in its history? The company was eventually acquired by Macy's in 2005.
Answer: Marshall Field's
- What is the name of the richest "city" (technically a "village" with a population of ~9,000) in the Chicago area, #10 on the overall US cities list, with an average income of $340,000? It's surrounded by three other high income communities, Highland Park, Northbrook, and Winnetka.
Answer: Glencoe
- 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
- What chain of breakfast cafes has over 190 worldwide locations, began at the intersection of two streets in downtown Chicago, and is now headquartered in Dallas? The chain features a black-and-white logo.
Answer: Corner Bakery Cafe
- Navy Pier was given its current name to honor the seafaring veterans of what war?
Answer: World War I
- 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
- 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
- "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
- 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 what large American city was home to the paper's headquarters. What was this city?
Answer: Chicago
- The name "Chicago" is derived from a French rendering of the Native American word Shikaakwa, which is what type of food?
Answer: Onion
- 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
- The Devil Baby of Hull House is an urban legend that is said to have inspired what 1967 Ira Levin horror novel and its film adaptation?
Answer: Rosemary's Baby
- 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
- 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 this man's surname?
Answer: Burnham
- In the 2000s, Walmart planned to build a chain of smaller discount stores focused on small towns and space-constrained cities in Arkansas, North Carolina, and Chicago. What "speedy" word was the planned name for this chain of stores?
Answer: Walmart Express
- What “K” psychology professor at the University of Chicago and Harvard came up with six stages of moral development that a person goes through? His staes include morality for personality benefit, morality conforming to social norms, and finally morality that best works for everyone.
Answer: Lawrence Kohlberg
- 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
- What singer-songwriter wrote and sang a song about infamous serial killer John Wayne Gacy on his 2005 double-album titled "Come On! Feel the Illinoise!" The biggest hit from the album was simply titled "Chicago."
Answer: Sufjan Stevens
- Featuring four rows of keys, the Chicago Theatre's massive organ was made by what "W" company from Germany?
Answer: Wurlitzer
- 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
- 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
- If you had a ticket to the World's Fair (the Columbian Exposition) in 1893, you'd be visiting what American city?
Answer: Chicago
- The building regarded as the world’s first skyscraper, the Home Insurance building, was built in 1884 in which American city?
Answer: Chicago
- In 1903, The International Brotherhood of Teamsters was created out of the merging of the Teamsters National Union (from Chicago) and the Team Drivers' National Union (from Detroit), and the headquarters was established in what Midwest U.S. city?
Answer: Indianapolis, IN
- 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 this woman and her husband partnered with another couple to launch a brand that debuted at Bergdorf Goodman in New York City.
Answer: Bobbi Brown
- Deemed the second best podcast of 2020 by The Atlantic, what is the name of the true crime podcast that follows Shapearl Wells as she investigates the 2016 murder of her son in Chicago?
Answer: Somebody
- The Chicago Blackhawks most recently won the Stanley Cup in 2015, defeating what Eastern Conference team in the finals?
Answer: Tampa Bay Lightning
- Within 3 percent, what percent of the total population of Illinois lives in Chicago?
Answer: 21% (18% - 24% accepted)
- 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
- 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
- Nicknamed "Commy" or "the Old Roman," what American man helped form the American League, owned one of its teams, and was inducted into the Baseball Hall of Fame in 1939?
Answer: Charles Comiskey
- 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
- 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
- What founding member of Chicago left the band in the 1980s to pursue a solo career, scoring a number-one hit on his own with "Glory of Love," the theme from "The Karate Kid?"
Answer: Peter Cetera
- 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
- In which decade did Chicago most recently have a Republican mayor?
Answer: 1930s
- Despite its name, which Chicago-based insurance company isn’t just for financiers?
Answer: Bankers Life
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About the Author
Eli Robinson is the Chief Trivia Officer at Water Cooler Trivia. He was once in a Bruce Springsteen cover band called F Street Band.
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