Established in 1922, this alley is one of a handful worldwide to still offer the old tradition of live pinsetters. The warning ("Don't bowl if you see legs") should be taken seriously. Put a rolled-up dollar in one of the holes of your ball and gently roll it down the alley. This little tip is most appreciated and can drastically improve your game. The vintage bar is delightful with pool tables, an arcade, a sidewalk café, great microbrew beers, and sandwiches.

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Double Door

This large space features up-and-coming national and local talents. The sound system is excellent, and so is the beer selection. A wooden dance floor is available if the mood strikes you, and the downstairs Dirt Room offers pool tables and arcade games. The atmosphere is very casual, and sight lines are good. Enter through the door by the alley on Damen Avenue.

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Empty Bottle

With atmosphere befitting a lounge or neighborhood pub, not to mention rock-bottom prices, this slightly dingy spot is a favorite with locals. Wednesday features avant-garde jazz, and Thursday through Saturday, local and national acts take over. Sunday is devoted to DJs. A small pool table and arcade area set behind the bar prove distracting to patrons, and a wonderful selection of beer and booze flows constantly. Earplugs are sold at the bar – the place can get a little loud.

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Local artwork and an incredible internet jukebox keep this Wicker Park favorite busy into the wee hours of the morning. The Irons's bars serve everything a thirsty patron could hope for. Pool tables add to the appeal. Stick around and watch because the crowd triples after 2am.

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Attempts to appear seedy only partially veil this club's polished interior, and yuppies and tourists often show up. The mellow blues joint offers jam sessions on Monday nights, and local acts perform Sunday through Thursday. Friday and Saturday, then, showcase national artists. A plethora of memorabilia fills the cavernous room, and pool tables and a Southern kitchen that's open till midnight keep patrons satisfied. Despite its touristy reputation, the club is a great place to see live blues in comfort.

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Goose Island Brewing Co.

Long hours at the grind got you thirsty for a home brewed beer? Head to this pub that crafts its own ale – over 10 homemade brews on tap. Try the signature drink, Honker's Ale, featuring a rich malt middle and a gentle hop finish. The bar also includes a small food menu with traditional eats, wings, barbecue, sandwiches, fries, burgers, etc. Want to learn about brewing? Take a tour of the Clybourn Brewery, provided every Sunday. Tastings after the tours are included.

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This Irish Pub is situated right next to "Nevin's Live," the pub's sister live music venue. The pub draws a mix of people, including many students from nearby Northwestern University. Irish food and drinks, including British and Irish ale, stout, and Guiness are available. Fish and chips and other Irish eats can be had. Pool tables and dart boards keep things lively, and the fireplace casts a cozy spell on the place.

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This sports bar draws a diverse mix of folks, who enjoy meeting up with friends and lingering over conversation on the outdoor, Olympic-themed deck during warm weather. Friday nights bring out karaoke singers, and nightly drink specials are added enticement. The large interior also offers pool tables.

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This Tex-Mex style bar features a prickly name and a list of interesting drinks. Try the lizard lemonade (vodka, lemonade, and a glow in the dark lizard to name just a few ingredients), the swamp water (vodka, apricot brandy, melon liqueur, 7-Up, orange juice, and sour mix), or one of the many martinis that line the menu. Notable martinis include the lemon drop, sparky, or tootsie roll. A hodge-podge of games as well as TVs provide nightly entertainment for the youngish professional crowd.

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Timothy O'Toole's Pub Chicago
Photo courtesy of Jill Heilemann

Timothy O' Toole's is a bustling sort of place that features a number of entertainment options – TV's, pool tables, dartboards, interactive trivia games, video games, and of course, the drink menu that includes microbrews as well as domestic and imported beer both on tap and by the bottle. Keep in mind, this place stays rather busy. In fact, they've poured more than 4 million pints of beer and served more than 150 tons of wings since opening in 1992.

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