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Trivia nights by city

A Chicago Trivia Night, Cubs and Sox Welcome

Lake wind outside, a full room and ten good questions inside.

Chicago is a city you hear before you see: the El grinding its curve over the Loop, a lake wind that finds the gap in every collar, a bus sighing at a corner three-flat where somebody's porch light has been on since 1962. In January the lake steams like a kettle. In July the whole city seems to live on its stoops and rooftops, arguing about pizza with the confidence of people who have never once been wrong.

It is a neighborhood town, and neighborhoods need somewhere to meet. So on a Tuesday, when the sidewalks are salted and the Bears have already broken someone's heart, people push through a heavy door into a warm back room, claim a table, name their team something they will regret, and wait for a quizmaster to clear their throat. A trivia night here is part civic duty, part grudge match, and the Cubs fans and Sox fans sit at the same tables.

This is the city that taught the country how to do improv and gave the blues its electric voice. That did not happen by accident. It happened because people kept showing up on weeknights for the hosts, the bands, the comics and the quizmasters, and a room full of strangers kept deciding to laugh together. Keep showing up.

Running a trivia night Chicagoans will come back for

Chicago crowds are loyal, loud and proud of their city, so a local round is the easiest win you have. The Cubs and White Sox split is good for at least one question and one friendly heckle. The Great Fire, the Columbian Exposition, the river that runs backward and the architecture of the Loop all make strong material, and food rounds (deep dish against tavern-style thin crust, Italian beef, the ketchup question) will start arguments you want.
Mind the rhythm. Winter is peak indoor season and weeknights fill up; summer brings patio nights and street festivals, so start later. Check the Bears schedule before booking a Sunday or Monday, and keep playoff nights for watching, not quizzing.

Why a live host still matters in Chicago

Put a speaker in the corner and people talk over it. Put a person with a microphone there and they read the crowd, lets the table that named itself after a Cubs curse enjoy its moment, and keeps the pace brisk when the lake wind has everyone tired. That is a craft, and Chicago has a long tradition of people who practice it well, on comedy stages and bandstands as much as at quiz nights.
So tip your quizmaster, stay for the second set, and go see the improv show your friend keeps mentioning. Want to run one yourself? Borrow the Chicago round on this page for your opener. The questions are the easy part; showing up every week is the job.

A free Chicago trivia round

Ten questions about Chicago, free to use at your next trivia night. Read them out as they are, or load the round into Trivia Show Maker to add it to a full show and print the answer sheets.

  1. The Great Chicago Fire broke out in which year?
  2. Which Great Lake forms Chicago's eastern shoreline?
  3. Name both of Chicago's Major League Baseball teams.
  4. What is the name of the North Side ballpark famous for its ivy-covered outfield walls?
  5. Every St. Patrick's Day, Chicago dyes what bright green?
  6. The mirrored sculpture in Millennium Park known as "The Bean" has what official name?
  7. Which condiment does Chicago tradition say must never go on a Chicago-style hot dog?
  8. Michael Jordan won six NBA championships with which Chicago team?
  9. Which ride, named after the engineer who built it, was the star attraction of Chicago's 1893 World's Columbian Exposition?
  10. Chicago's Sears Tower was renamed in 2009. What is it called now?
Show the answers
  1. 1871
  2. Lake Michigan
  3. The Cubs and the White Sox
  4. Wrigley Field
  5. The Chicago River
  6. Cloud Gate
  7. Ketchup
  8. The Chicago Bulls
  9. The Ferris wheel
  10. Willis Tower

Load this round into Trivia Show Maker Browse full trivia shows

More cities: New York · Toronto · Vancouver · Montréal · All cities
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  • Trivia Store
    • Halloween
    • Music Bingo Card Downloads
    • Free Song Lists
    • Trivia Nights by City
    • Eras
    • Pre-made Trivia Shows
    • Music Bingo & Trivia Bundles
    • Virtual Events
  • Featured!
    • Triv 101
    • Trivia Show Maker
    • BingoCardGenerator.Online
  • Our Games
    • Becoming A Game Show Host
    • Music Bingo
    • Fat Bottom Trivia >
      • Music Trivia Party
      • Sports Pub Night
  • Bingo Card Maker
    • Free Generator
    • Generator Pro (Lifetime Access)
    • All-Purpose Generator
    • Music Bingo Rules
  • Blog
  • Contact