for trivial pursuits
Okay, smarty-pants, let's see if you can get this one: What makes Grace O'Malley's Thursday-night pub trivia (8pm) better than the rest? Is it because (a) it's free to compete; or (b) the prize is a free bar tab for the entire team, the whole night? Answer: Both. And if you got our trick question, you shouldn't have any trouble kicking ass when it counts, so order drinks liberally. 1416 S Michigan Ave between 14th and 16th Sts, 312-588-1800.
The teams at this Tuesday-night pub quiz (8pm) know they have to be up on sports, movies, geography and music if they're going to win. They also know to pace their alcohol consumption because the more you drink, the less you think. But most important, they know to spread the word—the prize money depends on how many people play, and at $5 per person, winners could end up with drinking money for days. 3471 N Elston Ave at Albany Ave, 773-473-5263.
Sick of those pencil-and-paper trivia joints? Head to this homey, Cheers-style Jefferson Park watering hole where every table gets its own TV that broadcasts trivia questions. Winners score "Boom Bucks" that buy T-shirts, beer mugs and the like. Trivia is played Wednesdays and Thursdays at 8pm, but you can plug in the bar's Nintendo to the TVs anytime to feed your gamer addiction. 7607 W Addison St between Oriole and Ottawa Aves, 773-625-4116.