A trivia night is an easy way to meet people in Chicago: a set evening, a small team at one table and time to talk between rounds. We only list trivia nights that announce their dates on their own page or channel, or on the page of the venue that hosts them.
The trivia nights at a glance
| Trivia night | Venue | Roughly when | Teams | Cost |
|---|---|---|---|---|
| Whaddayaknow? Free Pub Trivia | Several bars, such as The Getaway (Lincoln Square) and Fatpour (Wicker Park) | Wed 8:30 pm at The Getaway, Mon 7 pm at Fatpour | Not stated | Free (2026) |
| Top Hat Trivia | Mary Jo McGuire's, Lincoln Park | Wed 7 pm | Not stated, new teams welcome | Usually free at public trivia nights (2026) |
| Pen & Paper Trivia | Central Park Bar, Avondale, and other bars | Tue 7 pm at Central Park Bar | Not stated | Free (2026) |
| Stewpendous Productions | Several bars, such as Whiskey Girl Tavern, Roscoe Village Pub and Motel Bar | Mon 7 pm, Tue 7 pm, Thu 6 pm, depending on the bar | Not stated | Not stated |
| Deep Cuts Horror Trivia | The Brewed, Avondale | About once a month on a Thursday, 7:30 pm | Not stated | Not stated |
| Pub Trivia at the University Pub | University Pub, Ida Noyes Hall, Hyde Park; guests come with a member | Tue 8 pm | Up to 8 | $3 a person (2026) |
| Trivia Tuesdays at Crust Tap Room | Crust Tap Room, Irving Park | Tue 7 pm | Up to 8 | Free (2026) |
| Tuesday Trivia at ERIS | ERIS Brewery and Cider House, Irving Park | Tue 7 to 9 pm | Not stated | Free (2026) |
| Trivia Night at Federales | Federales, Logan Square | Wed 7 pm | Not stated | Not stated |
| Monday Night Trivia Nights at Fathom | Fathom, Lakeview | Mon, sign-up from 7 pm, start 7:30 pm | Not stated | Free (2026) |
"Not stated" means we found nothing about it, not that the evening costs money or that teams have a fixed size.
The trivia nights one by one
Whaddayaknow? Free Pub Trivia (Lincoln Square, Wicker Park)
Whaddayaknow? Free Pub Trivia hosts trivia at several bars, and the bars call it free (2026). The Getaway in Lincoln Square has it on Wednesdays from 8:30 to 10:30 pm; an earlier date shows how the bar announces it. Fatpour in Wicker Park has listed it on Mondays at 7 pm, as an earlier date at Fatpour shows; check the bar's calendar for the next one. The bars give no team size and don't say whether you can join a team on your own, so ask beforehand.
Top Hat Trivia (Lincoln Park)
Top Hat Trivia hosts trivia at Mary Jo McGuire's in Lincoln Park on Wednesdays at 7 pm; its page for the bar shows the schedule and the results of past games. New teams are welcome; the page mentions no reservation, so come early. Public trivia nights are usually free (2026). The page gives no team size. In a post of its own, Top Hat says that at DMK Burger Bar in Lakeview, on Thursdays at 7 pm, you can bring a team or come solo; it doesn't say whether you'll be put on a team. Top Hat Trivia, Mary Jo McGuire's
Pen & Paper Trivia (Avondale)
Pen & Paper Trivia is a local quiz maker. At Central Park Bar in Avondale it runs a recurring series on Tuesdays at 7 pm. It also hosts trivia at other bars, such as Beat Kitchen in Roscoe Village, where an earlier date was free (2026) and 21 and over. Team size isn't given, and how you sign up depends on the bar and the date; check with the quiz makers or the venue. If you're coming alone, ask beforehand whether a team has room. Central Park Bar, trivia
Stewpendous Productions (several bars)
Stewpendous Productions runs bar trivia and special themed nights. According to its own Chicago trivia calendar, there are recurring dates on Mondays at 7 pm at Whiskey Girl Tavern, on Tuesdays at 7 pm at Roscoe Village Pub and on Thursdays at 6 pm at Motel Bar, among others. You pick the date and the bar in the calendar. It gives no team size or price. Stewpendous Productions, calendar
Deep Cuts Horror Trivia (Avondale)
Deep Cuts Horror Trivia is a themed trivia night at The Brewed, a café in Avondale, about once a month on a Thursday at 7:30 pm; the dates are in the café's calendar. For one edition the café wrote that you could come solo and be put on a team; ask whether that holds for the next one. The calendar gives no team size or price and mentions no reservation, so come early. The Brewed, events
Pub Trivia at the University Pub (Hyde Park)
The University of Chicago's events calendar lists Pub Trivia at the University Pub in Ida Noyes Hall on Tuesdays at 8 pm. A game lasts up to two hours, teams have up to eight people, and entry cost $3 a person (2026). According to its own page, the University Pub is a private membership club for people affiliated with the university and open to those 21 and over; guests must be accompanied by a member. The listing doesn't say whether you can join a team on your own, so ask beforehand. University of Chicago, events
Trivia Tuesdays at Crust Tap Room (Irving Park)
Crust Tap Room in Irving Park holds Trivia Tuesdays every week at 7 pm, free (2026). Teams have up to eight people, and the three best teams win prizes. The bar suggests getting a table early; it doesn't say whether you can join a team on your own. Crust Tap Room, Trivia Tuesdays
Tuesday Trivia at ERIS (Irving Park)
ERIS Brewery and Cider House in Irving Park has trivia every Tuesday from 7 to 9 pm, free (2026). You can reserve a table through Resy. ERIS gives no team size and doesn't say whether you can join a team on your own. ERIS, Tuesday Trivia
Trivia Night at Federales (Logan Square)
Federales in Logan Square holds a trivia night every Wednesday at 7 pm, with prizes for the winning teams. Federales offers table reservations and gives no entry price or team size. Federales, Trivia Night
Monday Night Trivia Nights at Fathom (Lakeview)
Fathom in Lakeview has trivia every Monday: sign-up from 7 pm, the game starts at 7:30 pm. In the bar's own words, Think or Swim Queer Trivia alternates with themed trivia nights. It's free (2026) and 21 and over. Fathom gives no team size. Fathom, Monday Night Trivia Nights
How to find your trivia night
- Coming alone: Deep Cuts Horror Trivia has offered to put solo guests on a team, and Top Hat Trivia welcomes solo players at DMK Burger Bar. Elsewhere, ask beforehand or at the bar whether a team has room.
- Team size: Up to eight at Crust Tap Room and at the University Pub.
- Day of the week: Fathom, Fatpour and Whiskey Girl Tavern on Mondays; Crust Tap Room, ERIS, the University Pub, Central Park Bar and Roscoe Village Pub on Tuesdays; Federales, Mary Jo McGuire's and The Getaway on Wednesdays; Motel Bar, DMK Burger Bar and Deep Cuts Horror Trivia on Thursdays.
- Age: Fathom and the University Pub are 21 and over, and so was the Pen & Paper date at Beat Kitchen.
- Kind of trivia: Horror at Deep Cuts, Think or Swim Queer Trivia and themed nights at Fathom, special themes at Stewpendous Productions.
- Signing up: Reservations through Resy at ERIS and through OpenTable at Federales, sign-up from 7 pm on the night at Fathom, membership or a member to come with at the University Pub; at Crust Tap Room, Top Hat Trivia and Deep Cuts, come early for a table.
After the trivia night
The best times to talk are between rounds and after the answers are read aloud. Simple openers work: "Do you come here often?", "Which question bugged you most?", "Do you know another good trivia night?" And if everyone on the team got along well, make plans to meet at the next one.
For people who run a quiz
If you run a quiz like these, you know the moment after the answers when the teams head off without swapping numbers. before is a web app for organisers. At the start you show the QR code on your phone; guests check in with it in their browser, without installing an app, and anyone who likes takes a selfie. The day after, the afterparty is open from 10 am to 8 pm. Anyone who shared a selfie sees everyone else who shared one there and can press the button for meeting again for up to five people. At 8 pm everyone finds out at the same time who wants to see each other again, and only then does a chat open. One-sided wishes stay invisible, and nobody receives a rejection. Nobody needs a profile. More on the page before for organisers.