Chicago History

Sports

100

Which Chicago Bulls player was named the NBA’s youngest MVP in 2011

Derrick Rose 

200

Which legendary Chicago Bears running back was known as "Sweetness" and is widely regarded as one of the greatest players in NFL history?

Walter Payton

300

Which Chicago Bears quarterback led the team to the Super Bowl in 2007

Rex Grossman

400

Which Chicago Blackhawks player is considered one of the greatest American-born hockey players and has been a key figure in three Stanley Cup victories

Patrick Kane

500

Largest NBA basketball Arena in the USA

United Center

Music

100

Who is the Chicago rapper known for his activism in the city, winning three Grammys in 2017 for his mixtape Coloring Book

Chance the Rapper

200

Which Chicago-born rapper's song "Lucid Dreams" became a breakout hit, blending hip-hop and emo music?

Juice World

300

Which Chicago-born rapper and producer is known for albums like The College Dropout and Graduation and has won over 20 Grammy Awards

Kanye West

400

What is the name of the Chicago music festival, held annually in Grant Park, that has become one of the largest music festivals in the U.S.?

Lollapalooza

500

Which Chicago native, often referred to as the "King of Soul," was known for hits like “A Change Is Gonna Come” and “Wonderful World”?

Sam Cooke

Politics

100

Which former U.S. President began his political career in Chicago as a community organizer?

Barack Obama

200

Who was the first African American mayor of Chicago, serving from 1983 until his death in 1987?

Harold Washington

300

Who was the longest-serving mayor in Chicago history

Richard J. Daley (1955-1976)

400

What was the infamous 1968 event that saw clashes between police and protesters during the Democratic National Convention in Chicago

The 1968 Democratic National Convention riots

500

Which Chicago-based political group was formed in the late 1960s as a response to systemic racial inequality and famously clashed with the city's police force

Answer: The Black Panther Party (Illinois chapter)

Neighborhoods

100

Which Chicago neighborhood was once known as the "Black Metropolis" during the Great Migration and is famous for its role in jazz and African American culture

Bronzeville

200

Which South Side neighborhood is home to the DuSable Museum of African American History, one of the oldest museums dedicated to Black history in the U.S.?

Washington Park

300

What Chicago neighborhood is named after the river that flows through it and was once the industrial center of the city?

River North

400

What South Side neighborhood is famous for its Irish heritage and hosts the South Side Irish Parade annually?

Beverly

500

Which neighborhood has a large number of Ethiopian and Eritrean restaurants and is known as “Little Africa”?

Uptown/ Rogers Park

Important Dates

100

March 4, 1837

Chicago Becomes a City

• Chicago was officially incorporated as a city. This was a key milestone in the development of what would become one of the largest cities in the United States.

200

October 8-10, 1871

the Great Chicago Fire

• The Great Chicago Fire destroyed much of the city, killing an estimated 300 people and leaving over 100,000 residents homeless. The fire is a turning point in Chicago’s history, as the rebuilding process transformed the city into a hub of architectural innovation.

300

July 27, 1919

Chicago Race Riot

• A racial conflict broke out after the drowning of a Black teenager, Eugene Williams, at a segregated beach. The riots left 38 dead and over 500 injured. This was part of the broader "Red Summer" of 1919, and the event highlighted the racial tensions in northern cities.

400

October 28, 1998

The Opening of Millennium Park

• Millennium Park officially opened to the public. It quickly became one of the most visited urban parks in the U.S. and a cultural symbol of modern Chicago, featuring iconic works like Cloud Gate (The Bean) and the Jay Pritzker Pavilion.

500

February 22, 1983

Harold Washington Elected Chicago's First African American Mayor

• Harold Washington was elected as the first Black mayor of Chicago, marking a significant milestone in the city's political and civil rights history. His election symbolized a shift in the city’s political dynamics and was a victory for Chicago's African American community.