If you want to pay lots of money in exchange for being asked increasingly obscure and intellectual questions that will leave you hunched over the bar counter, drunk, broke, and brainless, Hyde Park is the place you’re looking for. The University of Chicago Pub, in the basement of Ida Noyes (1212 E. 59th), hosts an intensely competitive trivia night every Tuesday at 8pm that requires participants to draw upon their knowledge of Malaysian geography, Romantic novelists, and theoretical physics, as well as the trivia standards of one-hit wonders and Bears scores. The rewards are high–a cash prize for first place, in addition to random free appetizers and Pub merchandise–but they come at a price: each participant must pay $3 to enter, and the bar is open only to University affiliates and their guests after buying a $10 membership or paying a $3 cover.
For those who’d rather spend their money on booze, the South Side has other options. Simone’s, in Pilsen (960 W. 18th), is a good one–their extensive beer list, which rotates seasonally, includes regional brews like Chicago’s own Metropolitan as well as imported favorites, and the kitchen pairs bar food standards with surprising aiolis. Their weekly trivia night, also on Tuesdays at 8pm, is run by the national franchise Team Trivia, whose questions skew more towards Oscar nominations and medical jargon. With trivia nights throughout Chicago, Team Trivia encourages league play, which will eventually bring the top twenty teams to a to-the-death tournament. (Full disclosure: I play for Simone’s home team, Fueled by Milk Stout and Sparkles, and we’re in it to win it.)
Bridgeport’s Schaller’s Pump (3714 S. Halsted) strikes a balance, with a $1 entry fee but questions cooked up behind the bar. The problem is that it’s a once-a-month event, on the third Tuesday (of course) at 7pm. And Buffalo Wings and Rings (3434 S. Halsted) has computerized trivia, but–much like the beer–why go for that when you can have the real thing?