A bartender prepares a margarita at The Matchbox. (Hilary Higgins / For RedEye )
The Matchbox 770 N. Milwaukee Ave. 312-666-9292
Looks like: The scene in the original "Willy Wonka and the Chocolate Factory" in which Gene Wilder walks through a room that impossibly becomes narrower and narrower
Smells like: Inside, not much; but the sidewalk cafe catches the occasional ribbon of exhaust from busy Ogden Avenue
Sounds like: Bubbles of cocktail-fueled conversations from squished-together couples who think they're whispering
Unlike New York, Chicago is a city in which you have some space to breathe. This is good news when it comes to finding apartments, strolling down sidewalks and maybe spotting a front lawn every now and then. But it also means that we rarely find ourselves in those romantic, cramped bars the size of a walk-in closet, where the sheer lack of square footage turns dimly lit strangers into intriguingly intimate conversation partners. I've always wondered whether this forced nearness is responsible for New Yorkers' supposed knack for chance encounters, as well as for their well-documented paranoia.
Chicago does have one bar, though, that could rival New York's most cramped confines. The Matchbox is Chicago's smallest social petri dish at an impossible 460 square feet. Next door to the metallic train car that is the Silver Palm diner, this 70-plus-year-old watering hole feels electric with history and mystery. Full disclosure, though: After even one of the potent, oversized cocktails served here, nearly everything feels electric.
As for those cocktails, to say they're well-priced is a gross understatement. Classics such as a Moscow mule, Manhattan or gimlet run you only $8.50—and they're giant. I always ask the no-nonsense bartenders for a gin gimlet, which they pour into a confectioners' sugar-rimmed martini glass and serve along with the shaker that contains extra liquid. After I finish my first drink (and am feeling a bit fancy), I practice my best bartender's shake to coax the final drops of liquid from the vessel into my glass. No matter how many trips I've made to this bar, I'm always slightly giddy when I realize that I have nearly an entire second cocktail left—woe to those who think they'll be ordering multiple gimlets, and even more woe to those hanging out with me after I've done just that.
Once the warm wood-paneled room begins to take on that special two-drinks-in glow, I become less defensive of the tiny barstool fortress I've created for myself. On a recent visit, I move my giant purse fence and watch as an, uh, uninhibited woman makes out with the side of a man's face. Despite our close proximity, the rest of the crowd seems unfazed. New couples fidget with the edges of their napkins, wondering what it means that they've stayed out so late with each other. Old friends debate the merits of the The Doors song on the stereo, and I'm tempted to chime in with my preference for "People are Strange." The Matchbox, with its generous drinks and non-existent personal space, practically requires I make just this sort of interruption.