Nobody likes a know-it-all, unless you're at a bar and it’s trivia night and he's on your team and there's an $800 cash prize on the line. Then EVERYBODY likes a know-it-all. If you've got one, definitely bring him to one of these: the five best bar trivia nights in Chicago.
North Center When: Tuesdays at 8pm If the New York Times crossword puzzle were a trivia night, this would be it. Long heralded as one of Chicago’s toughest trivia nights (quizmaster Dave has been at it for 10 years), it will have you trying to identify pictures of Madonna and Theodore Roosevelt with no hair, as well as tackling obscure trivia topics like "Dead or Canadian?". Specials: $4 Estrella Damm, $5 Belhaven, $1 off Flying Dog Prizes: Gift cards, charity donations
Lincoln Park When: Tuesdays at 8pm The Granddaddy of local trivia nights entertains a typically packed house with seven trivia rounds, including sports, stock symbols, news items (i.e. "According to Forbes, who was the highest-paid female actress of 2013?"), famous Halloween homes, and identifying the sets of TV shows, whether it's Friends or Fresh Prince of Bel-Air. Specials: $12 & $18 rotating pitchers Prizes: $800 cash prize for first place, plus $1,000 in raffle prizes
Lincoln Park When: Wednesdays at 9pm For a more laid-back, less competitive trivia scene, head to one of the North Side’s oldest bars, where you'll have to identify music based on audio snippets, answer newsy questions like, "what was the number one box office movie of last week?", and know a shload of Greek letters. Get there early for the free 8:30pm wings/food buffet. Specials: $10 Miller/Bud Light pitchers, $4 well drinks Prizes: Pitcher/round of shots for winner, runner-up picks category next week
Ukrainian Village When: Mondays at 8pm One of the newer entries to the ever-expanding trivia scene delves deep into your TV knowledge with one round dedicated to binge-worthy TV shows (Walking Dead, Breaking Bad...) as well as news items and a picture round where you’ll ID corporate logos and album covers. Play anywhere in the bar and listen in from loudspeakers. Specials: $3 Point drafts, $4 Stoli drinks Prizes: Concert tickets, gift cards ($40, $25, $10)
Lincoln Park When: Wednesdays at 8pm One of the more lively trivia nights keeps it classy by forcing you to identify 10 Britney Spears songs, name the brand of 10 purses based on photos, and get down with a theme sometimes -- like horror film trivia for Halloween. If that fails to keep you entertained, there's always their house Flabongo. Yes, it's a flamingo beer bong. No, we’re not kidding. Specials: $10 Miller/Coors pitchers, $10 any pizza, $14 New Belgium pitchers Prizes: $150 cash first prize, $100 cash second prize, 25% off your bill third prize
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Jay Gentile is the publisher of Chicago INNERVIEW Magazine and a Thrillist contributor. Follow him on Twitter.