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100

The name of the baseball team that plays on the South Side of Chicago

What is the White Sox?

100

When compared to normal pizza, Chicago style deep dish is unique because of this ingredient being on top. 

What is tomato sauce?

100

Lil Durk’s OTF stands for...

What is 'Only The Family'?

100

This man was the first black mayor of Chicago and has a large library, a city college, and several other things named after him.

Who is Harold Washington?

100

Besides being called the Windy City, Chicago is often referred to as this secondary nickname.

What is the Second City OR City of Big Shoulders OR Chi-town?

200

The name of the current Los Angeles Lakers All-Star that grew up in Chicago

Who is Anthony Davis?

200

The Chicago hot dog consists of a steamed Vienna beef hot dog, a poppy seed bun, a tomato, celery salt, sport peppers, a pickle, neon green relish, chopped onions, and this condiment.

What is (Yellow) Mustard?

200

This genre of electronic/club/dance music was founded in Chicago

What is House OR Footwork?

200

This famous gangster is known for running the city during the era of Prohibition and his involvement in the St. Valentine’s Day Massacre. 

Who is Al Capone?

200

The name “Chicago” is from a native american word that refers to this vegetable that is known to make you cry. 

What is an onion?

300

The name of the Chicago Women’s Basketball Team

What is the Chicago Sky?

300

This Chicago chain that serves Chicken is a favorite of both Common and Kanye and is known for its Mild sauce.

What is Harold's

300

This is the King of Soul, born in Mississippi raised in Chicago

Who is Sam Cooke?

300

This structure located downtown, on the Magnificent Mile, is known as one of the things that survived the Great Chicago Fire. 

What is the Chicago Water Tower?

300

This street in the city is the longest connected street in the world and is named after one of the four cardinal directions. 

What is Western Avenue?

400

The name of the Chicago Women’s Soccer Team

What is the Chicago Red Stars?

400

This famous Chicago chain is known for serving Chicago-style hot dogs, Italian beef sandwiches, chopped salad, cheese fries, homemade chocolate cake, and a chocolate cake shake.

What is Portillo's?

400

This legendary funk/disco/soul/pop band that got their start in Chicago, and are famous for the Hit ‘September’

Who are Earth, Wind, and Fire?

400

This is the man who founded Chicago; he has a history museum, a bridge, and many other things named after him

Who is Jean Baptiste Point du Sable?

400

Michigan Avenue, known for its shopping and other tourist attractions, is often called this glamorous nickname. 

What is the Mag Mile OR Magnificent Mile?

500

The number of Punts and Kickoffs Bears legend Devin Hester returned for Touchdowns over the course of his 8 year career with the Bears

What is 18?

500

Garrett Popcorn has a Chicago style mix that consists of caramel popcorn and this orange-colored variety.

What is cheddar OR cheese popcorn?

500

This Chicago Rapper is also a member of the Rock Band Japanese Cartoon

Who is Lupe Fiasco?

500

Chicago lies on land belonging to the Council of the Three Fires; the name of one of the three native groups that make up the Council is..

Who are the Ojibwe OR Odowa OR Potawatomi?

500

The city’s train system is known as the “L” because of this unique feature that sets it above others. 

What is being elevated OR elevation?

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