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Only in Chicago
100

This former First Lady grew up on the South Side and later helped bring the Obama Presidential Center to Chicago’s Jackson Park

Who is Michelle Obama?

100

This downtown park is home to the famous sculpture nicknamed “The Bean.”

What is Millennium Park?

100

This holiday movie begins with a Chicago-area family accidentally leaving Kevin behind.

What is Home Alone?

100

This major fire in 1871 destroyed much of Chicago and became one of the most famous events in the city’s history.


What is the Great Chicago Fire?

100

Chicagoans may say they’re going to “The Jewel” when they mean this grocery store.

What is Jewel Osco?

200

This talk show host became one of the most influential media figures in the world after launching her show from Chicago

Who is Oprah?

200

This underground downtown maze is where GPS goes to die, rideshares get confused, and Batman chase scenes make sense.

What is Lower Wacker Drive?

200

This 1980 comedy follows Jake and Elwood on a “mission from God” through Chicago.

What is The Blues Brothers?

200

This man became Chicago’s first Black mayor in 1983.

Who is Harold Washington?

200

After a snowstorm, this controversial Chicago tradition involves saving a shoveled parking spot with chairs, cones, crates, or random household items.

What is dibs?

300

Chairman of the Illinois Black Panther Party, known for organizing across racial lines through the Rainbow Coalition.

Who is Fred Hampton?

300

This North Side beach is where people go to play volleyball, show off dogs, take skyline pics, and pretend Lake Michigan is the ocean.

What is Montrose Beach?
Alternative: North Avenue Beach

300

This comedy centers on a South Side barbershop and stars Ice Cube and Cedric the Entertainer.

What is Barbershop?

300

This man, of African descent, is widely recognized as the founder of Chicago.

Who is Jean Baptiste Point du Sable?

300

This one-letter name refers to Chicago’s elevated train system.

What is the L?

400

This comedian from Chicago’s South Side starred in a syndicated comedy and was one of the “Original Kings of Comedy.”

Who is Bernie Mac? 

400

This South Side neighborhood is known as Chicago’s historic “Black Metropolis.”

What is Bronzeville?

400

This 1970s sitcom follows a Black family living in a Chicago housing project.

Answer: What is Good Times?

400

In 1968, this major political event in Chicago became known for protests, police violence, and national controversy.

What is the 1968 Democratic National Convention?

400

This South Side chicken chain is famous for mild sauce and big portions.

What is Harold’s Chicken?

500

This Chicago poet became the first Black author to win the Pulitzer Prize

Who is Gwendolyn Brooks?

500

The horror classic "Candyman" is strongly tied to the now-demolished public housing development on the Near North Side.

What is Cabrini-Green?

500

This sitcom gave us Steve Urkel and was set in Chicago.

What is Family Matters?

500

Legend says this animal started the Great Chicago Fire, though historians doubt the story.

What is Mrs. O’Leary’s cow?

500

This Bridgeport spot is one of Chicago’s most iconic old-school hot dog stands, known for the original Maxwell Street Polish.

What is Jim’s Original?