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100

What is the name of the natural history museum located on Chicago's Lake Shore Drive?

The Field Museum

100

What is the name of the Chicago riverfront area that features numerous bars, restaurants, and entertainment options?

River North

100

What is the nickname for Chicago's professional hockey team?  

The Chicago Blackhawks

100

What is the name of the Chicago cultural center located in a historic Beaux-Arts building?

The Chicago Cultural Center

100

Who was the first African American President of the United States, with strong ties to Chicago?

Barack Obama

200

In what year did the Chicago Cubs last win the World Series before their 2016 victory?

1908

200

What is the oldest public zoo in the United States, located in Chicago?

Lincoln Park Zoo

200

What Chicago neighborhood is famous for its annual "Bud Billiken Parade"?

Bronzeville

200

What is the name of the historic theater on State Street that hosts musicals and performances?

The Chicago Theatre

200

 Which Chicago-born actress starred in movies like "The Dark Knight" and "Mystic River"?

Maggie Gyllenhaal

300

Which Chicago park is home to the annual Taste of Chicago food festival?

Grant Park

300

What famous Chicago landmark was once known as the "Sears Tower"?

Willis Tower

300

What is the nickname for Chicago's elevated train system?

The "L"

300

Which Chicago skyscraper features a distinctive diamond-shaped top?

The Smurfit-Stone Building (formerly the Stone Container Building)

300

Who is the famous Chicago-based talk show host known for her daytime television show?

Oprah Winfrey

400

Which famous gangster was responsible for the St. Valentine's Day Massacre in Chicago?

Al Capone

400

Which Chicago street is known for its high-end shopping and luxury boutiques?

The Magnificent Mile (Michigan Avenue)

400

What is the official tree of Chicago?

The White Oak

400

Which Great Lake does Chicago border?

Lake Michigan

400

Which Chicago blues musician was known as the "Father of Chicago Blues"?

Muddy Waters

500

What famous 1980 movie was filmed in Chicago and features the "Blues Brothers"?

"The Blues Brothers"

500

What Chicago neighborhood is home to the Museum of Science and Industry?

Hyde Park

500

What is the name of Chicago's professional baseball team on the South Side?

The Chicago White Sox

500

What is the name of the underground tunnel system used for freight transportation in Chicago?

The Chicago Freight Tunnels

500

Which Chicago-born comedian and actor starred in "Home Alone" and "Uncle Buck"?

John Candy

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