Chicago Sports
Chicago Food
Chicago Landmarks
Famous Chicagoans
Chicago History
100

This NBA team has won six championships, all during the 1990s. 

Who are the Chicago Bulls?

100

This Chicago staple is deep-dish and loaded with toppings. 

What is deep-dish pizza?

100

This 1,450-foot-tall building was once the tallest in the world. 

What is the Willis/Sears Tower?


100

This former US President began his political career in Chicago. 

Who is Barack Obama?

100

This 1871 disaster destroyed much of Chicago, leading to a massive rebuilding effort. 

What is the Great Chicago Fire?

200

This MLB team broke a 108-year championship drought by winning the World Series in 2016.

Who are the Chicago Cubs?

200

This sandwich consists of thinly sliced beef served on a hoagie roll, often dipped in au jus.

What is an Italian beed sandwich?

200

This famous park is home to "The Bean".

What is Millennium Park?

200

This talk show queen and media mogul got her start in Chicago.

Who is Oprah Winfrey?

200

Chicago was incorporated as a city in this year. 

What is 1837?

300

The Blackhawks play this sport and have won multiple Stanley Cups.

What is hockey?

300

A Chicago-style hot dog is famously served without this common condiment. 

What is ketchup?

300

Chicago's Field Museum is home to one of the most complete T. Rex skeletons ever discovered, named this. 

Who is Sue?

300

This Chicago rapper's debut album The College Dropout launched him to fame in 2004, and he later became one of the most influential figures in both music and fashion. 

Who is Kanye West? 

300

This infamous Chicago gangster ruled the city's underworld during Prohibition.

Who is Al Capone?

400

This NFL team's only Super Bowl win was in 1986, with the help of their "Super Bowl Shuffle."

Who are the Chicago Bears?

400

This popcorn mix is caramel and cheese popular, and known as what?

What is the Chicago Mix?


400

This neo-Gothic skyscraper, completed in 1925, was designed by the architectural firm Howells & Hood and is known for its flying buttresses and crown-like peak. 

What is the Tribune Tower?

400

Known for his charitable work and unique blend of gospel and hip-hop, this Chicago rapper won three Grammys in 2017 for his mixtape Coloring Book.

Who is Chance the Rapper?

400

This 1893 event, held in Chicago, celebrated the 400th anniversary of Christopher Columbus' arrival in the Americas and showcased innovations like the Ferris wheel. 

What is the World's Columbian Exposition?

500

This soccer team shares a name with one of the city's historic events.

Who are the Chicago Fire?

500

Originating in Chicago, this 1930s creation combines soft drink syrup with carbonated water. 

What is the Green River soda?

500

This art museum houses Grant Wood's famous painting "American Gothic."

What is the Art Institute of Chicago?

500

This Chicago rapper is famous for his drill music and tracks like "Love Sosa" and "I Don't Like," which helped popularize the drill movement in the early 2010s. 

Who is Chief Keef?

500

Chicago's population grew significantly due to this 19th-century transportation innovation. 

What is the railroad?

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