Chi Artists
Windy City History
Chi-Town Sports
Chicago Slang
Landmarks
100

This female rapper from Chicago gained viral attention for her bold lyrics and confident persona, and is known for her songs "Baked as a Pie" and "My Way".

Who is Queen Key?

100

This fiery disaster of 1871 nearly wiped Chicago off the map... but out of the ashes rose the city’s modern skyline.

What is The Great Chicago Fire?

100

Before becoming a global basketball icon, this man led the Chicago Bulls to six NBA championships in the 1990s.

Who is Michael Jordan?

100

This three-letter abbreviation refers to Chicago’s scenic expressway along Lake Michigan, famous for its views of the skyline.

What is LSD (Lake Shore Drive)?

100

Located on the lakefront, this pier is home to rides, restaurants, and a famous Ferris wheel.

What is Navy Pier?

200

This Chicago rapper and activist once said, “I met Kanye West, I’m never goin’ to fail.”

Who is Chance the rapper?

200

Elected in 1983, this mayor’s campaign slogan, “It’s Our Turn Now,” symbolized a new era of Black political power in Chicago as its first Black mayor.

Who is Harold Washington?

200

This historic stadium on the North Side of Chicago is home to the Cubs.

What is Wrigley Field?

200

You ain’t really from the city if you never caught a ride on this elevated train system.

What is the “L”?

200

This South Side Chicago neighborhood, also known as Parkway Gardens, is famous in hip-hop culture and is referenced by rappers like Chief Keef and King Von.

What is O-Block?

300

This Chicagoland born rapper, known for hits like Lucid Dreams and All Girls Are the Same, tragically passed away in 2019 at the age of 21.

Who is Juice WRLD?

300

This 1919 event began after a young Black boy drowned due to racial segregation at a Lake Michigan beach, sparking citywide unrest.

What is The Chicago Race Riot of 1919?

300

This WNBA team brought a championship back to the city in 2021, led by Chicago-born star Candace Parker.

What is Chicago Sky?

300

This Chicago condiment, a blend of ketchup, barbecue sauce, and hot sauce, is a staple on fried chicken and fries in the city’s Black food scene.

What is mild sauce?

300

Once the tallest building in the world, this iconic Chicago skyscraper was originally called the Sears Tower.

What is the Willis Tower? 

400

Known for his fast flow and hits like Slow Jamz and Overnight Celebrity, this West Side rapper is one of the fastest in the game.

Who is Twista? 

400

Known as the “Black Metropolis,” this historic South Side neighborhood was the center of Black business, music, and culture in the early 20th century.

What is Bronzeville?

400

He was of the greatest running backs of all time who played in the NFL for 13 seasons with the Chicago Bears, known as “Sweetness.”

Who is Walter Payton?

400

When someone is lying or exaggerating, Chicagoans say they are doing this.

What is cappin’?

400

The famous public park in the Loop with Buckingham Fountain at its center.

What is Grant Park?

500

This Chicago-born rapper, actor, and activist started his career in the 1990s and is known for songs like “The Light” and “I Used to Love H.E.R.”

Who is Common?

500

This Chicago-based newspaper, founded in 1905, played a key role in spreading news and empowering the city’s Black community.

What is The Chicago Defender?

500

After a 108-year drought, this Chicago baseball team finally broke the curse and won the World Series in this year.

What is 2016?

500

This term is used to call someone silly, awkward, or acting dumb in Chicago slang.

What is goofy?

500

Famously nicknamed "The Bean", this reflective bean-shaped sculpture in Millennium Park is one of Chicago’s most photographed attractions.

What is Cloud Gate?