Chicago History
Chicago Architecture
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Chicago Music
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100

In what year did the Great Fire occur?

1871

100

What was the original name of the Willis Tower?

Sears Tower

100

Known as the Main Street of America, which two-digit “route” starts in Chicago?

Route 66

100

What long-running Broadway musical features songs like "All That Jazz," "Cell Block Tango," and "Mr. Cellophane?

Chicago The Musical

100

Who are the “Monsters of the Midway”?

The Chicago Bears

200

Ike Sewell and Richard Riccardo invented the Chicago deep dish at what pizzeria?

Pizzeria Uno

200

Which neo-Gothic tower, built in 1925, sits on N Michigan Ave?

Tribune Tower

200

What famed Chicago-based improv theater group gets its name from one of Chicago’s many nicknames?

Second City

200

Which Chicago blues legend opened a club in Chicago because of a promise made to keep the Blues alive?

Buddy Guy

200

What was Michael Jordan’s Jersey Number when he played for the Chicago Bulls?

23

300

The stars on the Chicago flag represent: Fort Dearborn, the Great Fire, the World's Columbian Exposition of 1893, and what else (year)?

The World’s Fair of 1933

300

Which Chicago landmark was the largest building in the world from 1931 to 1943?

Merchandise Mart

300

What Chicago-based book follows dual plot lines of the architecture of the 1893 World's Fair and the serial killer Dr. H. H. Holmes?

The Devil in the White City

300

Also known as "The Chairman of the Board," who sang that Chicago was his "kind of town?"

Frank Sinatra

300

Which famous Chicago tavern put a curse on the Chicago Cubs?

Billy Goat Tavern

400

What was the original name of O’Hare International Airport (ORD)?

Orchard Place Airport/Orchard Field

400

One of the most famous landmarks in Chicago, which fabled structure survived the Great Fire?

The Chicago Water Tower

400

Which native Chicagoan was the father of the “happiest place on earth”?

Walt Disney

400

Which Chicago band gets its name from its founder’s astrological sign?

Earth, Wind, and Fire

400

Most recently, the Chicago Blackhawks won the Stanley Cup in what year?

2015

500

After the Great Fire, what did the citizens of the United Kingdom send to the city of Chicago?

8,000 books

500

Chicago’s streets are designed on a grid. At what intersection does Chicago’s grid begin?

State and Madison

500

Which Chicagoland suburb is Frank Lloyd Wright’s home and studio located in?

Oak Park

500

Chicago native Jennifer Hudson won both an Oscar and a Golden Globe for her performance in what 2006 musical film?

Dreamgirls

500

Who is known as the “Original Bull”, retired Bull’s player number 4?

Jerry Sloan

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