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100

This Chicago-born tennis player won 7 Grand Slam titles and was known for her rivalry with Martina Navratilova.

Chris Evert

100

This reflective public sculpture in Millennium Park is often nicknamed "The Bean."

Cloud Gate

100

The Chicago River was famously dyed green for the first time St Patties Day in what decade? (Hint: it was in the 1900s) 

1960's

100

This west suburb is famous for the Frank Lloyd Wright Home and Studio.

Oak Park

100

This band is named after the city and has hits like “Saturday in the Park.”

Chicago

200

Known for his iconic #34 jersey, this Hall of Fame Bears running back was nicknamed "Sweetness."

Walter Payton

200

This massive convention center on Lake Michigan is the largest in North America.

McCormick Place

200

1968, this major political convention took place in Chicago and was marked by massive protests.

Democratic National Convention

200

This suburb shares its name with a U.S. president and is home to a well-known outlet mall.

Lincolnshire

200

Finish this "Go Cubs Go" lyric, 

[Verse 2]
They got the power
They got the speed
To be the best... ________

300

This pioneering architect rebuilt much of Chicago after the Great Fire and is often called the “father of skyscrapers.”

Louis Sullivan

300

This legendary blues club on North Halsted has hosted icons like B.B. King and Buddy Guy.

Buddy Guy’s Legends

300

The Great Chicago Fire started in this decade

1870s (1871 to be specific) 

300

This western suburb was a major center for the Underground Railroad and abolitionist activity.

Wheaton

300

"Sweet Home Chicago” became an anthem of the blues and was famously performed in this 1980 film.

The Blues Brothers

400

$100: This famous Chicago-born writer chronicled the city’s South Side in Native Son.

Richard Wright

400

This rotating restaurant atop the former John Hancock Center is now closed but was once a tourist favorite.

The Signature Room

400

The first televised U.S. presidential debate took place in Chicago between these two candidates.

John F. Kennedy and Richard Nixon

400

This suburb is home to Argonne National Laboratory, one of the oldest U.S. science and engineering centers.

Lemont

400

“Lake Shore Drive” is a 1970s song by this band that many mistake for praising LSD.

Aliotta Haynes Jeremiah

500

Before becoming a Supreme Court justice, this Chicago-born woman served as U.S. Solicitor General under Obama.

Elena Kagan

500

This former stockyard district once processed over 80% of U.S. meat and was known as “hog butcher for the world.”

Union Stock Yards

500

The phrase “The city that works” is often attributed to this long-serving Chicago mayor.

Who is Richard J. Daley?

500

This affluent North Shore suburb was once home to the headquarters of Kraft Foods.

Northfield

500

The 1995 musical, Chicago, based on death, greed, and jazz debuted at the Shubert Theatre before its Tony-winning revival. Name a song from the musical. 

Overture / All That Jazz, Funny Honey, Cell Block Tango, When You're Good to Mama, All I Care About, A Little Bit of Good, We Both Reached for the Gun, Roxie, I Can't Do It Alone, My Own Best Friend, Finale Act I, Entr'acte, I Know a Girl, Me and My Baby, Mister Cellophane, When Velma Takes the Stand, Razzle Dazzle, Class, Nowadays, Hot Honey Rag, Finale / All That Jazz (Reprise).

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