Sometimes known by the nickname "Scarface", this man was a notorious Chicago gangster during the Prohibition Era who served as the co-founder and boss of the Chicago Outfit.
Al Capone
This music festival is hosted in Grant Park every summer.
Lollapalooza
This landmark is 110 stories tall.
Willis Tower
Creator of the magazine, Playboy. He lived in a mansion.
Hugh Hefner
Wrigley Field is the center of this Chicago neighborhood.
Wrigleyville
This natural history museum has more than 10 acres of exhibits.
Field Museum
Chicago's first African American mayor. This man also has a downtown Chicago library named after him.
Harold Washington
This food festival is hosted every year, attracting more than 1.5 million visitors.
The Taste of Chicago
Which famous architect, known for his work on the Robie House and the Unity Temple, spent much of his career in Chicago?
Frank Lloyd Wright
Former First Lady of the United States and Whitney Young High School alum.
Michelle Obama
Loyola University's Lake Shore Campus is located in this neighborhood, just south of Evanston.
Rogers Park
Which Chicago park is home to the Buckingham Fountain, one of the largest fountains in the world?
Grant Park
This amusement park attraction was first introduced in Chicago as a landmark for the 1893 World Fair.
Ferris Wheel
The annual Chicago Christmas tree lighting takes place in this downtown Chicago Park.
Millennium Park
This sports arena, built in 1924, holds up to 61,500 spectators and owned by the Chicago Park District.
Soldier Field
A comedian known for his films Ghostbusters and Groundhogs Day. He also is a dedicated Cubs fan.
Bill Murray
The University of Chicago and the DuSable Museum of African-American History are located in this neighborhood.
Hyde Park
What Chicago museum houses a U-505 German submarine from World War II?
The Museum of Science and Industry
In what year was the first Chicago Cubs World Series championship?
1907 (They won again in 1908 and then famously in 2016 after a 108-year drought).
Chicago's yearly summer fireworks displays take place here.
Navy Pier
Built by Marshall Fields & Co, this downtown building takes up 2 city blocks and is known for its art deco design.
Merchandise Mart
Successful Hollywood actor who starred in blockbusters such as Star Wars and Indiana Jones
Harrison Ford
This predominantly Latin neighborhood is home to a variety of murals that stretch for 2 miles on 16th Street.
Pilsen
Which Chicago beach hosts the annual Chicago Air and Water Show?
North Avenue Beach
This man is considered the first non-indigenous permanent resident in Chicago, honored as "the founder of Chicago."
Jean Baptiste Point du Sable
The largest African American parade in the US, which has occurred on the second Saturday of August, since 1929.
The Bud Billiken Parade
Which Chicago architect is known for pioneering modern skyscraper design?
Louis Sullivan, often referred to as the “father of skyscrapers.”
This famous Hollywood legend and children’s filmmaker was born in the Hermosa neighborhood of Chicago.
Walt Disney
This neighborhood is home to St. Michael's Church, one the of the seven buildings to survive the Great Chicago Fire.
Old Town
What famous T. rex fossil is on display at the Field Museum?
Sue the T. rex, the most complete T. rex fossil ever discovered