City Cast Chicago logo
Display Ad: Children play near Chicago's Cloud Gate. "Big plans. Coming right up." with pizza graphic on left; "Enjoy Illinois. Meet in the middle." on right.

The Best Trivia Nights in Chicago

Posted on December 10, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

A crowd of people play trivia

Meet neighbors and regulars at trivia nights across the city. (gappleca / Flickr)

Hey Chicago readers and City Cast Chicago listeners love all types of games — including trivia. So we’re rounding up some of the best spots for (almost) every day of the week.

Sunday

Head to the newly renovated venue’s taproom for weekly trivia every Sunday from 7–9 p.m. This month’s trivia is all about the holidays ❄️ Yes, it’s open to all ages. Yes, it’s free to play. Yes, you can win prizes.

Monday

If you have a case of the Mondays, trivia night at this neighborhood bar should lift your spirits. Not to mention you can get a Miller High Life and a shot of Malört (or tequila or bourbon) for $7 …

City Cast

Why Does Chicago Love to Hate Malort?

00:00:00

Tuesday

Sidetrack in Northalsted

Fellow pop culture fans, this gay bar is the place to be to test your knowledge on everything from the “Real Housewives” franchises to “Wicked.”

Join Geeks Who Drink for weekly trivia, $15 pizza, and $5 pints of beer. Plus, South Side Weekly recently dubbed the pub the best place to unwind.

Eli Tea Bar in Andersonville

Chicagoans who want to play trivia in a nonalcoholic scene can go to this specialty tea shop for its popular trivia night.

Trivia sheet

You can go to trivia nights in Chicago almost every day of the week. (Growth + Co. / Unsplash)

Wednesday

Marz Community Brewing in McKinley Park

This South Side bar has some of the coolest programming and events in the city, which is why you will definitely catch us checking out their trivia night, too.

Thursday

Bucktown Pub in Bucktown

Get to the cozy neighborhood pub early to claim your spot for trivia, which kicks off at 8 p.m. Can’t make it in person? You can join remotely! Plus, a $100 cash prize is up for grabs every three weeks …

Facets in Lincoln Park

Chicago cinephiles, assemble! On the third Thursday of the month, compete to see how well you know different films. Then, stick around for a screening.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.
Advertisement image

The latest in Chicago

Neighborhood GuidesApril 23

Where to Read in Chicago

It’s National Library Week through April 25 — which is coincidentally Independent Bookstore Day! There’s an official crawl across Chicago...

A white building with pillars, on the street there are cars parked in front of it
Chicago, ExplainedApril 22

The End of an Era For Lincolnwood Town Center

Lincolnwood Town Center shuts down April 30 — depending who you ask. I went to the mall to check things out for myself.

Emmi Mack at Lincolnwood mall
Neighborhood GuidesApril 20

Celebrate 420 at These Chicago Dispensaries

It’s been a little over 6 years since recreational marijuana was legalized in Illinois. At the time, Gov. JB Pritzker called it the “most...

Three people standing in a room. In the back is art work. There are 4 paintings across, and 3 paintings down
Chicago, ExplainedApril 17

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events? Test yourself in our weekly trivia quiz.

A security officer and his dog at a CTA Blue Line Station
3 Questions WithApril 14

3 Questions With Chicago’s Poet Laureate

It’s National Poetry Month, and while you can find a variety of workshops and open mics in April, poets call Chicago home all year round.

A woman smiling while sitting. There is a potted plant in the back
Chicago HistoryApril 8

Who’s Preserving Chicago Family History?

If you are like me, all your family history lives within multiple photo albums and VHS tapes stored in your parents’ living room cabinets.

Group of adults and children sit in a circle around an infant lying down in a home
Food & DrinkApril 6

New Spots To Dine & Drink in Chicago

Chicago has no shortage of good places to eat around town. Here are some of the bar, restaurant, and café openings we're watching.

Chef Jake Schneider of Schneider Deli
Food & DrinkMarch 30

Hot Chicken in Chicago

Chicago has plenty of its own famous sandwiches, but the Nashville hot chicken trend is still going strong across the city.

Woman holds hot chicken sandwich in front of pink wall featuring large painted illustration of a chicken