Sports Arts and Entertainment People Places History
100
What is Derrick Rose?
This Chicago Bulls guard became the youngest MVP in NBA history at the age of 22
100
What is Lupe Fiasco?
This Chicago-born rapper, who performed at the Hill Auditorium in 2011, was responsible for such hits as "Kick, Push" and "The Show Goes On"
100
What is Barack Obama?
This Chicago-based politician authored the 2006 bestselling book "The Audacity of Hope"
100
What is Wrigley Field?
Known as "The Friendly Confines", this baseball field, located in Lakeview, is the second-oldest active Major League ballpark
100
University of Chicago
The world's first atomic reaction occurred at this Chicago area university in 1942
200
What is Jay Cutler?
Sid Luckman held the Chicago Bears' all-time record for passing yardage for 70 years before it was broken by this man in 2013
200
What is Evanston?
The 2004 film Mean Girls, which starred Lindsay Lohan, was based in this Chicago suburb.
200
What is Oprah Winfrey?
This Chicago native was the host of the highest-rated talk show in American television history and was named "The World's Most Powerful Woman" by both CNN and Time.
200
What is the Willis Tower?
This building, which was the tallest in the world from 1973-1998, was renamed to this in 2009
200
What is Mrs. O'Leary's cow?
According to urban legend, this animal was responsible for the Great Chicago Fire of 1871
300
What is 1908?
The Chicago White Sox won their first World Series championship in 88 years in 2005, a feat the Chicago Cubs haven't accomplished since this year
300
What is jazz?
The name of this genre of music, which originated in the African-American community and is characterized by a high degree of improvisation, first appeared in print in a Chicago newspaper
300
What is Hugh Hefner?
This University of Illinois graduate founded Playboy magazine in Chicago in 1953
300
What is Navy Pier?
This former military training center is Chicago's most popular tourist attraction
300
What is the Chicago Board of Trade?
This Chicago institution, founded in 1848, is the world's oldest futures and options exchange
400
What is the Calder Trophy?
Chicago Blackhawks' star Patrick Kane's career highlights include: assaulting a cab driver for not giving him his $0.20 in change, getting kicked out of a University of Wisconsin frat party for choking a girl, and winning this prestigious award in 2008
400
What is Second City?
This Chicago-based improv comedy troupe has an extensive list of famous alumni which includes Bill Murray, John Belushi, and Stephen Colbert
400
What is Rahm Emanuel?
The current and first Jewish mayor of Chicago, he was also Barack Obama's Chief of Staff from 2009-2011
400
What is Grant Park?
Known as Chicago's front yard, this park, named after a former U.S. president, hosts large festivals such as the Taste of Chicago and Lollapalooza
400
What is Stephen Douglas?
He was elected as Illinois's senator in 1858 after a series of now-famous debates which primarily focused on the issue of slavery
500
What is Ernie Banks?
Known as "Mr. Cub", this 14-time All-Star became the first player in Chicago history to hit 500 Home Runs
500
What is Ferris Bueller's Day Off?
This 1986 coming-of-age film, which was written by John Hughes and starred Matthew Broderick, notably featured many Chicago landmarks.
500
What is Frank Lloyd Wright?
This architect, who began his career in Chicago, was a leader of the Prairie School movement and developed the concept of the Usonian house
500
What is the Field Museum?
This place is the home of Sue, the largest and most complete Tyrannosaurus Rex ever discovered
500
What is the 18th Amendment (Prohibition)?
Evanston native Frances Willard was one of the leaders of the Women's Christian Temperance Union, which was largely responsible for the passage of this.






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