Chicago: The Matchbox

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The Matchbox
770 N Milwaukee Ave.
Chicago, Illinois
312-666-9292

Some dive bar aesthetes may try to disqualify the Matchbox because the bartenders know how to make so-called “fancy” drinks and stock an enticing array of high-end liquors. But why should a perfect Manhattan or a refined tequila be a bad thing? And where else in the world, let alone Chicago, can you find such a curious building? Despite its name, the Matchbox occupies a space shaped like a skinny pizza slice, gradually diminishing in width to only three feet. It’s like something out of a Charlie Kaufman movie. As significant an architectural site for the city’s West Town as the Flatiron Building is to Manahattan’s Herald Square, the Matchbox may be able to get you boozed up in style, but the regulars are a cantankerous bunch who will analyze your cocktail selection as a measure of moral integrity. So choose wisely. Then see if you are worthy to hang. Pay an afternoon visit, and you can hear these guys grouse about the yuppies and the kids (who usually prefer to drink on the makeshift sidewalk patio outside), the latest civic controversy or a Cubs loss. It’s the kind of vernacular poetry hometown journalistic heroes like Studs Terkel and Mike Royko reveled in: a real slice of Chicago.

Photos: James Trevenen

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