History
What was the name of the owner of the cow that started the Great Fire?
Mrs. O'Leary
Deep-dish gets the hype, but real Chicagoans are more likely to grab this thin, crispy, square-cut pizza from the corner bar.
What is Tavern Style/NY Thin Crust
What intersection is 0/0 on the grid?
What is State and Madison?
This 1930s Federal Art Project brought murals and sculpture into public spaces, linking art with social progress.
Which baseball player of any Chicago team has hit the most home runs in a season?
Who is Sammy Sosa?
During Prohibition, this bootlegging boss turned Chicago’s South Side into his personal empire.
Al Capone
This Italian-American creation, soaked in au jus and sometimes topped with giardiniera, reflects Chicago’s working-class immigrant roots.
The city’s segregation and housing discrimination were legally upheld until this 1966 campaign led by Martin Luther King Jr.
What is the Chicago Freedom Movement?
This Chicago institution helped launch the careers of countless comedians — and turned satire into an art form of social critique.
What is Second City?
What year was Wrigley Field built?
1916
The 1886 labor movement for the 8-hour workday turned bloody in this famous square — inspiring May Day around the world.
What is Haymarket Square?
This Chicago Jewish deli classic, featuring hand-sliced corned beef or pastrami on rye with mustard, became a staple on the North Side and reflects waves of Eastern European immigrants in the early 20th century.
What is a Jewish deli sandwich / pastrami on rye?
What street is Comiskey Park located at?
What is 35th?
Before “soul” had a name, this Chicago singer recorded A Change Is Gonna Come — a civil rights anthem as much as a song.
Who did Michael Jordan (and others) explicitly keep from playing on the Dream Team?
Who is Isiah Thomas?
This 1969 police raid killed Black Panther leader Fred Hampton — and exposed systemic racism in Chicago policing.
Who is Fred Hampton
Chicago’s Maxwell Street Market, famous for its smoky Polish sausages and blues buskers, was nearly destroyed during which controversial phase of “urban renewal”?
What is the University of Illinois at Chicago expansion in the 1960s?
What street is the Magnificent Mile on?
What is Michigan Ave?
Kanye West once wrote as song about Chicago, before he lost his mind. What was name of the woman in the song?
Who is Wendy?
This White Sox player got knocked out by Jose Ramirez, after talking a big game.
Who is Tim Anderson?
This 1983 mayor, the city’s first Black leader, fought both racism and the Chicago Machine before it was cool.
Who is Harold Washington
What are the toppings of a Chicago style hot dog?
What is, poppy seed bun, vienna beef dog, mustard, sweet relish, onions, tomato wedges, peppers, celery salt, dill pickle spear
This massive infrastructure project reversed a river — and symbolized Chicago’s willingness to reshape nature for industry.
This Chicago-born rapper blurred the line between gospel and hip-hop on his album Coloring Book, creating a sound rooted in faith and community rather than corporate labels.
These two catchers (one Cub and one Sox) came two blows in a titanic clash at home plate.
Who are Michael Barret and AJ Pierzynski?