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Simon’s Tavern

The neighborhood’s Swedish history lives on in this worn-and-warm tavern, which dedicates one whole wall to a deer-hunting mural featuring regulars from years past. There are also goblets of seasonal…

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Delilah’s

Any lived-in, urban dive that pays homage to Joe Strummer, pinball and whiskey in equal measure, could be a potential classic. Delilah’s—dark, friendly and loud—is. It boasts more than 600…

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Cole’s

An offbeat, welcoming joint surrounded by craft breweries and fancy cocktail houses, Cole’s is a throwback that hosts revolving art exhibits, variety shows, live bands and a mentalist. It also…

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Carol’s Pub

The clientele at this rowdy 4 a.m. country bar is unlike any other in Chicago. Old winos, yuppies, cougars, college kids and urban hillbillies all come together to dance and…

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The Matchbox

The Matchbox is a Chicago institution that dates to the 1990s, well before mustachioed mixologists entered the scene. This is the kind of place where classic Collinses are still mixed…

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Bangers & Lace

This sausage (the bangers) and beer (the lace—a term for the doily of suds left after drinking down a beer) place comes with its own cicerone, who curates the rotating…

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Big Star

A little slice of Austin in Wicker Park, Big Star is about as country as Chicago gets—which is to say, not very. Vintage neon and a vinyl soundtrack are the…