Landmarks
Bonus Questions
Famous People
Music
100

Chicagoans call the Willis Tower by its former name.

What is the Sears Tower?

100

He was the host of Jeopardy for 37 seasons since 1984.

Who is Alex Trabek?

100

Known for bootlegging and the St. Valentines Day Massacre this gangster was arrested for tax evasion.

Who is Al Capone?

100

During the 7th inning stretch at the Cubs games Harry Caray would sing this song from 1908.

What is "Take Me Out to the Ballgame"?

200

This building that towered over Michigan Avenue was the home of a newspaper.

What is the Tribune Tower?

200

This nickname for Chicago originated from weather conditions or politicians filled with hot air.

What is the Windy City?

200

A Chicago mayor once lived in Cabrini Green. 

Who is Jane Byrne?

200

In 1980 The Blues Brothers performed this song on stage.

What is Sweet Home Chicago?

300

The expressway that runs alongside the shoreline of Lake Michigan is often called the outer drive.

What is Lake Shore Drive?

300

This group of Chilean students are UChicago Alumni that were taught by Milton Friedman and Arnold Harberger in the 70's and 80's.

Who are the Chicago Boys?

300

This father and son were both Mayors of Chicago. 

Who are the Daleys?

300

Born in Chicago, this singer and actress was a finalist on American Idol. 

Who is Jennifer Hudson?

400

The train that runs through Chicago is commonly called a letter in the alphabet.

What is the "L"?

400

An American TV host created Jeopardy and The Wheel of Fortune.

Who is Merv Griffin?

400

The train was created for dancers by South-sider Don Cornelius.

What is Soul Train?

400

The best known version of this song was performed by Frank Sinatra in the late 50's. 

What is Chicago (That Toddlin' Town)?

500

In 1893 The Columbian Exposition was held in a park named after a president.

What is Jackson Park?

500

Since 1969, the United States flag hangs from the pole 24/7, 365 days a year and never comes down at this location.

What is the Moon?

500

The 44th President of the United States also taught at the University of Chicago.

Who is Barack Obama?

500

The lyrics "Will you still love me for the rest of my life?" was sang by what musical group in 1986?

Who is Chicago?

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