Chicago Quiz

Try out this Chicago quiz to test your knowledge. Chicago trivia spans a city shaped by rapid growth, architectural innovation, immigrant communities, and a long-standing influence on American music, food, sports, and politics.

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15 questions

~3 min to finish

Easy to hard difficulty

440 pts max score

Question 1 · Medium · 20 pts
Which major music festival turns Chicago’s Grant Park into a huge concert venue?
Question 2 · Medium · 20 pts
Which blues legend became a major figure in Chicago’s music scene?
Question 3 · Hard · 40 pts
Which structure, completed in 1885, is often singled out as the first skyscraper?
Question 4 · Hard · 40 pts
Who co-authored the 1909 Plan of Chicago?
Question 5 · Hard · 40 pts
What settlement house, founded in Chicago in 1889 by Jane Addams, is the answer here?
Question 6 · Hard · 40 pts
Name the politician who became Chicago’s first Black mayor in 1983.?
Question 7 · Hard · 40 pts
Which Chicago labor conflict is tied specifically to the year 1886?
Question 8 · Hard · 40 pts
Which Prohibition-era figure is identified here as a leading Chicago gangster?
Question 9 · Hard · 40 pts
Who wrote the poem “Chicago,” the one that calls the city “Hog Butcher for the World”?
Question 10 · Hard · 40 pts
Who published the first Playboy issue in Chicago in 1953?
Question 11 · Hard · 40 pts
Which North Michigan Avenue landmark opened in 1925?
Question 12 · Easy · 10 pts
Chicago is the largest city in which U.S. state?
Question 13 · Easy · 10 pts
Chicago sits along the southwestern shore of what lake?
Question 14 · Easy · 10 pts
Which NFL team calls Chicago home?
Question 15 · Easy · 10 pts
Which NBA team is based in Chicago?

Which major music festival turns Chicago’s Grant Park into a huge concert venue?

Which blues legend became a major figure in Chicago’s music scene?

Which structure, completed in 1885, is often singled out as the first skyscraper?

Who co-authored the 1909 Plan of Chicago?

What settlement house, founded in Chicago in 1889 by Jane Addams, is the answer here?

Name the politician who became Chicago’s first Black mayor in 1983.?

Which Chicago labor conflict is tied specifically to the year 1886?

Which Prohibition-era figure is identified here as a leading Chicago gangster?

Who wrote the poem “Chicago,” the one that calls the city “Hog Butcher for the World”?

Who published the first Playboy issue in Chicago in 1953?

Which North Michigan Avenue landmark opened in 1925?

Chicago is the largest city in which U.S. state?

Chicago sits along the southwestern shore of what lake?

Which NFL team calls Chicago home?

Which NBA team is based in Chicago?