Chicago: A trivia powerhouse, from Wicker Park dives and Logan Square arcades to Lakeview beer gardens and downtown sports halls.
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A friendly West Ridge neighborhood tap pouring since 1972, with 16 beers on tap, free pool on a 9 foot Diamond table, and a back patio. Chicago Pub Mix Trivia runs the room every Tuesday at 7:30, free to play for teams of five or fewer, with goofy prizes and 5 dollar shots to get the brain working.
View venue & vote →Chicago's Big House, a 40 year Lakeview institution for Michigan and Detroit sports fans, runs free Pen and Paper trivia every Wednesday with prizes for the winners. Old-school rules: no phones, no screens, just decent questions.
View venue & vote →A family-owned East Lakeview dive with two roomy bar areas, free pool, and dart boards, plus a kitchen that punches well above its dive-bar looks. Monday nights at 7, Twin City Trivia runs the room with a host the regulars rave about, which makes it a genuinely good reason to look forward to a Monday.
View venue & vote →A classic Southport Corridor dive with fantastic wings, cheap pitchers, and an independent trivia night that brings out neighborhood loyalists.
View venue & vote →Home of the eight dollar Chicago Handshake, this Avondale corner spot runs free music trivia with Pen and Paper on the 1st, 3rd, and 5th Tuesdays: albums, artists, and your favorite and least favorite earworms, with prizes for the winners.
View venue & vote →Everything in this vintage-stuffed Avondale lounge is for sale except the trivia. Pen and Paper hosts a free general-knowledge night on the last Sunday of the month, with prizes for the winners and a Pierogi Papi pop-up keeping the table fed.
View venue & vote →The Chicago outpost of the famed New York cocktail bar pours serious drinks in Avondale, with happy hour 365 days a year. Pen and Paper trivia takes over on the 3rd Monday of the month, free with prizes, and some of the city's best bartenders may be playing against you.
View venue & vote →A Lakeview corner tavern open since 1986 and known for its giant stash of board games, the kind of place where neighbors become friends. Bar trivia runs every Tuesday at 7, free to play, and there is a Jeopardy style bar league on Thursdays with cash and gift card prizes.
View venue & vote →A Lakeview tiki bar where Sunday nights move to the Back Room for a Jeopardy style bar league, presented by Geeks Who Drink and hosted by Justin Parlette, who entertains as much as he quizzes. First place takes $200 cash, and every team that makes it to Final Jeopardy is entered in a $200 raffle, win or lose. Great bar food and cheap drinks round out the night.
View venue & vote →An Andersonville barcade packed with vintage cabinets, pinball, and a busy drag and events calendar on North Clark. Stewpendous Productions runs free trivia every Wednesday at 7, with tab credit for the top teams, so you can settle up the night on your winnings. Games, drinks, and a quiz with real personality.
View venue & vote →A no-frills West Town corner bar on Chicago Avenue with stiff pours, a pool table, and a neighborhood-regulars feel. Geeks Who Drink runs its multimedia quiz every Wednesday at 8, with bar cash for the sharpest teams. Cheap drinks, a laid-back room, and a quiz that brings out the locals.
View venue & vote →Widely known as one of Chicago's premier soccer bars, this expansive British pub transforms into a fiercely competitive trivia battleground on Tuesday nights.
View venue & vote →An eco-friendly Pilsen staple built from repurposed architectural salvage, featuring a massive Tuesday night crowd and excellent craft cocktails.
View venue & vote →A beloved Wisconsin-themed sports bar famous for its cheese curds, Muskie decor, and a packed midweek quiz it runs itself. A true Lakeview institution.
View venue & vote →A historic, multi-level corner tavern in Bucktown that draws a big neighborhood crowd to kick off the week with trivia and pizza specials.
View venue & vote →Renowned for its incredible outdoor patio and extensive craft beer list, this Lakeview icon hosts a premier Tuesday trivia night.
View venue & vote →Famous for its whole-animal service and a great beer garden, this West Town destination puts an upscale culinary spin on pub trivia.
View venue & vote →A massive subterranean sports bar near Navy Pier with over 70 TVs and a robust, high-energy trivia night favored by downtown workers.
View venue & vote →A spacious South Loop pour house boasting over 60 craft beers on tap and a heavily attended Thursday night trivia session.
View venue & vote →Directly across from Second City, this expansive Irish pub serves hearty comfort food alongside a lively end-of-week quiz.
View venue & vote →A sports bar famous city-wide for its award-winning wings, the perfect pairing of comfort food and Thursday night trivia.
View venue & vote →A vibrant neighborhood soccer pub on Chicago Avenue known for its fantastic patio and a highly competitive Wednesday trivia night.
View venue & vote →A cornerstone sports bar on Division Street known for wood-grilled burgers, drink specials, and a loud, competitive pub quiz.
View venue & vote →A sprawling, multi-level sports bar in Wicker Park featuring giant glass keg coolers and a rowdy Wednesday trivia scene.
View venue & vote →An upscale sports lounge in River North with an elevated food menu and a popular, fast-paced trivia night (reservations recommended).
View venue & vote →A refined neighborhood pub in Edgewater serving excellent craft beer and hosting a heavily attended midweek Sporcle game.
View venue & vote →A massive, traditional neighborhood pub with a heated beer garden and a staple Wednesday-night trivia crowd.
View venue & vote →Holding the second-oldest liquor license in Chicago, this historic South Loop tavern is a classic, intimate setting for Monday-night trivia.
View venue & vote →A cozy, unassuming neighborhood gem tucked into the West Loop with great food and a highly competitive Sporcle league.
View venue & vote →A rustic, wood-paneled tavern on Belmont with a retractable roof upstairs, known for cheap pitchers and midweek trivia.
View venue & vote →A classic, dog-friendly neighborhood dive right beneath the Blue Line tracks, with a laid-back trivia vibe.
View venue & vote →A cozy Avondale cocktail-and-smashburger tavern that runs free general trivia every Tuesday from 7 to 9, with gift cards, swag, and free shots on the line. Bonus: on the first Sunday of each month, Paul of Pen and Paper Trivia hosts a themed night where players vote on next month's topic during the game.
View venue & vote →Roscoe Village's beloved music venue and kitchen hosts Pen and Paper Trivia as a roughly monthly pop-up, free to play with prizes for the winners. Dates move around from month to month, so check the venue calendar for the next one.
View venue & vote →An 8,000 square foot Lincolnwood sports bar with 200 plus beers and indoor curling lanes, running free Pen and Paper trivia every Tuesday. Prizes for the winners and no phones allowed, just decent questions.
View venue & vote →A lovingly restored 8-lane vintage alley with manual scoring and frozen White Russians, named Best Design at the World's 50 Best Bars 2024. Free Pen and Paper trivia lands on the 1st and 3rd Thursdays; dates occasionally shift, so check the calendar.
View venue & vote →Lincoln Park's clubhouse for game nights: free Pen and Paper trivia every Monday with prizes for the winners and free hot dogs for every player. Private karaoke rooms and a Saturday Jeopardy bar league round out the week.
View venue & vote →Seven thousand square feet of original tin ceilings, 60 plus taps, and spiked milkshakes in Roscoe Village. Free Pen and Paper trivia every Thursday with prizes for the winners and half-price pizza to start the week on Mondays.
View venue & vote →Avondale's beloved live-music hall hosts themed Pen and Paper trivia one Sunday a month, free to play, and winners never walk away empty handed. The theme rotates monthly, so check the calendar for the next edition.
View venue & vote →A dog-friendly Avondale patio bar where free Pen and Paper trivia runs every Tuesday with prizes for the winning teams, rotating food pop-ups, and question rounds that move out to the spacious patio in the warmer months.
View venue & vote →A small bar with a big personality: this neon-lit elevated dive hosts free music trivia with Pen and Paper on the 2nd and 4th Tuesdays, covering albums, artists, and more, with prizes for the winners and an annual chili cook-off on the side.
View venue & vote →A neighborhood taproom with a backyard patio that welcomes kids until 8 and dogs all night, plus rotating weekend food pop-ups. Pen and Paper trivia runs the 2nd and 4th Wednesdays, free to play with prizes for the winners and 5 dollar happy hour pints before game time.
View venue & vote →A woman-owned taquito bar with a fully gluten-free and nut-free kitchen, Kite String Cantina is about as welcoming as it gets. Sunday nights at 7 they run five rounds of cheerfully random trivia with Quizz Daddy Trivia, so grab a seat, order some hand-rolled taquitos, and bring your best useless knowledge. The bar leans local, with standout Chicago beers and agave-forward cocktails.
View venue & vote →A beloved North Center institution since 2005, Mrs. Murphy & Sons brings the warmth of a real Irish pub to Chicago. Thursday nights at 7:30 are reserved for pub trivia, a natural gathering for regulars and newcomers alike. With dozens of Irish whiskeys, scratch-made pub fare, and live music through the week, there is no cozier room to settle in for a quiz.
View venue & vote →A lively Lincoln Park sports bar with three full bars, a big year-round patio, and a full food menu. Every Wednesday at 7:30 they run a fan-favorite trivia night with prizes for the top three teams. Stick around for the burger, bourbon, and beer deal and you have got yourself a proper Chicago Wednesday.
View venue & vote →A dog-friendly Irving Park watering hole tucked under the Metra tracks at Grayland Station, the kind of neighborhood bar where the regulars know your name. On the first Thursday of each month at 7:30, a local solo host runs an original trivia night with clues written in-house. Cheap beer, a friendly room, and a fresh quiz for your crew.
View venue & vote →The Lincoln Park sister saloon to the legendary Butch McGuire's, opened in 2025 with maximalist vintage decor, handmade bar bites, and raucous live music upstairs at Mary Jo's LIVE. Every Wednesday, Top Hat Trivia runs trivia night, with 12 dollar pizzas and 50 cent toppings to fuel the brain. A buzzy, friendly room where the regulars know the bartenders by name.
View venue & vote →A self-described best-hidden gem in Bucktown, allegedly pouring since 1932, with free popcorn, a world-renowned private beer garden, and a dog-friendly welcome inside and out. Thrillhouse Trivia packs the house every Thursday at 8, so the regulars get there early to grab a seat. Cheap whiskey, fancy drafts, and a quiz worth showing up for.
View venue & vote →A legendary Uptown honky tonk pouring since 1972, all live country bands, line dancing, and Chicago Handshakes at the bar. Every Wednesday the room trades two-steps for trivia when Whaddayaknow runs a free pub quiz, so bring a team and prove your useless knowledge finally pays off. Cold beer, cowboy boots, and a genuinely one of a kind Chicago night.
View venue & vote →A friendly Ravenswood corner bar known for big burgers, cold drinks, and a wall of TVs for the game. Every Wednesday at 8, Kwizmaster Kirk runs trivia until last call, the kind of low-key weeknight quiz the regulars build their week around. Patio seating, weekend karaoke, and a welcoming neighborhood crowd.
View venue & vote →A one of a kind brewery incubator on Milwaukee Avenue where a rotating lineup of up-and-coming beer brands share the taps, so the lineup is never quite the same twice. Geeks Who Drink runs free trivia every Monday at 7, every player gets a free five ounce pour to start, and the winning team walks out with a gift card. A genuinely fun way to kick off the week in Logan Square.
View venue & vote →The Chicago outpost of the cult Brooklyn pizzeria, slinging wood-fired pies and a deep beer list on Milwaukee Avenue. Whaddayaknow runs free pub trivia every Thursday at 7, with Paulie Gee's gift cards on the line for the winning teams. Great pizza, cold beer, and a quiz worth building your Thursday around.
View venue & vote →A laid-back Logan Square spot on Armitage with a big patio and a kitchen worth lingering for. Brain Sportz Trivia takes over every Wednesday at 8, fueled by 2 dollar tacos, 2 dollar rose shots, and 3 dollar High Lifes to keep the team sharp. A reliably good midweek hang.
View venue & vote →A long-running Division Street bar in Wicker Park with a heated year-round patio and a serious cocktail list. The house runs free team trivia every Tuesday at 8, prizes included, the kind of low-key neighborhood night the regulars plan around. Strong drinks, a friendly room, and a quiz that pulls a crowd.
View venue & vote →A Logan Square watering hole right by the California Blue Line with a roomy patio and an easygoing crowd. Brain Sportz Trivia runs the room every Tuesday at 7:30, free to play with drink specials to keep things loose. A solid, unpretentious place to test what you know.
View venue & vote →A friendly Edgewater corner tavern on North Clark with stiff pours and a regulars-know-your-name vibe. Stewpendous Productions runs free trivia every Monday at 7, a low-key way to shake off the start of the week. Cheap drinks, a warm room, and a quiz worth showing up for.
View venue & vote →The legendary Northalsted video bar, a Boystown institution famous for its show-tune nights and sprawling multi-room space. Stewpendous Productions takes over every Tuesday at 8 for free trivia, no cover as always. An only-in-Chicago night out with a quiz to match.
View venue & vote →A cozy Roscoe Village neighborhood pub on Addison with a solid beer list and an easygoing crowd. Stewpendous Productions runs free trivia every Tuesday at 7, beer and trivia making the perfect midweek combo. An unpretentious local where the regulars take their quiz seriously.
View venue & vote →An Edgewater neighborhood spot on Broadway with a hearty menu and a warm, all-are-welcome feel. Stewpendous Productions hosts free trivia on Monday nights, a fun reason to start the week out right. Good food, good drinks, and a quiz run by one of Chicago's most beloved hosts.
View venue & vote →A massive Fulton Market playground of a bar with bowling, vintage arcade games, karaoke rooms, and a from-scratch kitchen. Stewpendous Productions runs free trivia every Tuesday at 7, with free chips and salsa to keep the table fed. Bring a big team and make a whole night of it.
View venue & vote →A cozy New East Side coffee and wine bar tucked along the north side of Lakeshore East Park, where morning espresso gives way to wine and live events come evening. Brain Sportz Trivia runs the room every Thursday at 6:30, an early-evening quiz that suits the downtown crowd. Warm woods, a flexible space, and a genuinely welcoming neighborhood feel.
View venue & vote →A welcoming Jefferson Park brewery taproom on Austin Avenue pouring its own beers, now slinging Pequod's deep-dish and hosting live jazz in the corner. The house runs free trivia every Thursday at 7 (inside only, so grab a table), a low-key Northwest Side night out. Good brews, good people, and a quiz worth the trek.
View venue & vote →A sprawling River North Irish pub on Grand Avenue, a go-to for Guinness, soccer matches, and a proper pub feel. Geeks Who Drink takes over every Wednesday at 7 with its seven-round multimedia quiz, bar cash on the line. Big screens, a big crowd, and a quiz with real personality.
View venue & vote →A friendly Roscoe Village gastropub on Roscoe Street with a deep beer list and a comfortable, all-are-welcome vibe. Geeks Who Drink runs free trivia every Wednesday at 7:30, seven rounds of audio, visual, and everything in between. A reliably fun midweek night in the neighborhood.
View venue & vote →No bars match.
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