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Windy City Celebrities Trivia Quiz

Chicago, founded in 1833, has produced many celebrities from all walks of life. How many of them do you know?

A multiple-choice quiz by aurorerio. Estimated time: 4 mins.

Author
aurorerio

Time
4 mins

Type
Multiple Choice

Quiz #
352,900

Updated
Dec 03 21

# Qns
10

Difficulty
Average

Avg Score
8 / 10

Plays
575

One at a Time - Single Page - Timed Game

Question 1 of 10

1. According to legend, this woman's cow kicked over a lantern that started the Great Chicago Fire in October 1871. What was her name? Hint

Mrs. O'Leary

Mrs. Fields

Mrs. Butterworth

Mrs. Crocker

NEXT>

Question 2 of 10

2. This beloved comedian, famous for perpetually being 39, was born in suburban Waukegan. Who was he? Hint

Bob Hope

Jack Benny

Charley Weaver

Ed Wynne

3. One of the most notorious gangsters of his time, this 1920s bootlegger's favourite hangout was the Green Mill, a bar that is still operating at Broadway and Lawrence Streets in Chicago. Who was he? Hint

Bugsy Seagal

Pretty Boy Floyd

Clyde Barrow

Al Capone

NEXT>

Question 4 of 10

4. This award-winning author, TV and radio personality and raconteur, lived to the age of 96, documenting much of 20th century Chicago. Who was he? Hint

Irv Kupcinet

Jack Brickhouse

Mike Royko

Studs Terkel

NEXT>

Question 5 of 10

5. Although born in Pennsylvania, this NFL coach will forever be known as the man who took "Da Bears" to the Super Bowl. Who is he? Hint

Jim Maura

Bill Cowher

Joe Gibbs

Mike Ditka

NEXT>

Question 6 of 10

6. A Chicago native son, he created "Playboy" magazine and spent the second half of the 20th century influencing American popular culture. What's his name? Hint

Hugh Hefner

Hunter S. Thompson

Bennett Cerf

Truman Capote

NEXT>

Question 7 of 10

7. Though born in the South, this media mogul has made Chicago her professional home since the 1980s. Who is she? Hint

Rosie O'Donnell

Martha Stewart

Oprah Winfrey

Ellen DeGeneres

NEXT>

Question 8 of 10

8. This popular actress, with a hit TV series on the Fox network, gained fame in a series of Christopher Guest films. Who is she? Hint

Catherine O'Hara

Jane Lynch

Parker Posey

Jennifer Coolidge

NEXT>

Question 9 of 10

9. This popular comedian of the 1960s and '70s was born and raised in Harvey, Illinois, a suburb south of Chicago. What's his name? Hint

Bob Newhart

Joe Flaherty

Harold Ramis

Tom Dreesen

NEXT>

Question 10 of 10

10. Elected Mayor of Chicago in 2011, he was previously Chief of Staff to President Barack Obama. Who is he? Hint

Rahm Emmanuel

George Stephanopoulis

Jesse Jackson, Jr.

Richard Daley

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Most Recent Scores

Nov 08 2024 : Johnmcmanners: 10/10
Oct 05 2024 : Guest 173: 10/10

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Quiz Answer Key and Fun Facts

1. According to legend, this woman's cow kicked over a lantern that started the Great Chicago Fire in October 1871. What was her name?

Answer: Mrs. O'Leary

Although popularized in the 19th and 20th centuries, there is no truth to this rumour and the City of Chicago officially apologized to the O'Leary family. No one knows for certain what caused the great fire in that year, but a combination of dry weather and high winds was responsible for it spreading so fast.

2. This beloved comedian, famous for perpetually being 39, was born in suburban Waukegan. Who was he?

Answer: Jack Benny

Jack Benny was always proud of his Chicago roots and visited his hometown often. He was fond of visiting the Pump Room restaurant and was always accessible to his many fans, and he was one of the most popular personalities on WGN radio.

Answer: Al Capone

Urban archeologists have discovered a network of underground tunnels below the Green Mill, where Capone and his men would hide from FBI agents.

4. This award-winning author, TV and radio personality and raconteur, lived to the age of 96, documenting much of 20th century Chicago. Who was he?

Answer: Studs Terkel

Studs Terkel won a Pulitzer Prize in 1984 for his book "The Good War", and lived for many years in the Uptown neighborhood on Chicago's north side.

5. Although born in Pennsylvania, this NFL coach will forever be known as the man who took "Da Bears" to the Super Bowl. Who is he?

Answer: Mike Ditka

Tough-talking Mike gave the world a winning football team, the Super Bowl Shuffle and a popular restaurant on Chicago's north side.

6. A Chicago native son, he created "Playboy" magazine and spent the second half of the 20th century influencing American popular culture. What's his name?

Answer: Hugh Hefner

Hef moved his "Playboy" headquarters into the old Palmolive skyscraper on Michigan Avenue. At the top of the building, there was a beacon that rotated at night. But when the John Hancock building went up in the 1970s, residents sued to have the light turned off so they could get some sleep.

7. Though born in the South, this media mogul has made Chicago her professional home since the 1980s. Who is she?

Answer: Oprah Winfrey

Oprah's Harpo Studios are on the near west side of Chicago. And many of Oprah's charitable pursuits have benefitted thousands of Chicago school children. For many years, she has maintained a residence on Michigan Avenue, Chicago's Magnificent Mile.

8. This popular actress, with a hit TV series on the Fox network, gained fame in a series of Christopher Guest films. Who is she?

Answer: Jane Lynch

Jane grew up in the south suburbs of Chicago. The other three also gained fame in Christopher Guest films, but are not from Chicago.

9. This popular comedian of the 1960s and '70s was born and raised in Harvey, Illinois, a suburb south of Chicago. What's his name?

Answer: Tom Dreesen

The other three are also popular Chicago area comedians, but not from Harvey.

10. Elected Mayor of Chicago in 2011, he was previously Chief of Staff to President Barack Obama. Who is he?

Answer: Rahm Emmanuel

Known for his combative personality, he has been given the nickname "Rahmbo".
Say what you will, Chicago politics has been producing Chicago celebrities for more than 100 years.

Source: Author aurorerio

This quiz was reviewed by FunTrivia editor bloomsby before going online.
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