Entertainment
Sports
History
Neighborhoods
Misc.
100

What former presidents started out as IL senators?

Barack Obama and Abraham Lincoln

100

What are the two baseball teams in Chicago?

The Cubs and the White Soxs

100
How many stars are in the Chicago flag?

Four

1) Fort Dearborn

2) The Great Chicago Fire

3 & 4) The World's Fair

100

What neighborhood is Intrinsic in?

Belmont Cragin

100

What is the name of the great lake that borders Chicago?

Lake Michigan

200

What famous Chicagoan was the host of her own TV show, TV network, and also a billionaire?

Oprah Winfrey

200

Where do the Bulls and Blackhawks play home games?

The United Center

200

What is the name of the public transportation system in Chicago?

The CTA aka Chicago Transit Authority

200

What neighborhood is known as La Villita? 

Little Village

200

For what holiday does Chicago dye the river green?

St. Patrick's Day 

300

What Chicago born rapper was famous for his 2018 hit song "Lucid Dreams” ? 

Juice WRLD

300

How many total sports teams does Chicago have 

Football: Bears, 

Basketball: Bulls and Sky

Hockey: Blackhawks

Baseball: Cubs and White Soxs

Soccer: Fire and Red Stars

300

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?

Cloud Gate

300

What neighborhood hosts the Puerto Rican day parade?

Humboldt Park

300

What is the name of the tallest skyscraper in Chicago (also the second tallest skyscraper in North America) 

Sears (Willis) tower

400
What is the name of the actress that has starred in hit movies like Akeelah and the Bee, Jump In, and the 2022 movie NOPE? 

Keke Palmer

400

What Chicagoan was the youngest-ever MVP in NBA history?

Derrick Rose

400

What baseball stadium in Chicago is the second oldest baseball stadium in the United States? 

Wrigley Field

400

What neighborhood is home to the only free zoo in Chicago?

Lincoln Park

400

What's the name of the famous T-Rex that lives in the Field Museum?

SUE

500

Chicago rapper, also known as Sosa, rose to fame with his song “I Don’t Like”

Chief Keef 

500

When was the last year the the Chicago Bulls won a championship? 

1998

500

After the Great Chicago Fire, Chicago is said to have built the first ever ____________?

Skyscraper 

500

What is the name of the park that hosts the Lollapalooza music festival? 

Grant Park

500

What are the colors of the different El lines? Hint: There are 7!

Red, Blue, Brown, Pink, Green, Purple, Yellow