Matchbox Bar

"Like oysters or puppies, great things come in small packages. And the same can be said for The Matchbox, one of the tiniest bars in town. What The Matchbox doesn’t have in space it makes up for in personality. You’ll literally struggle to get past other people sitting at the bar to get an open seat, but the friendly atmosphere will make you feel right at home. This is the kind of place where bartenders know the regulars, but they’ll be equally as friendly to any newcomers who walk in the door. Come with one other person to kick it over classic cocktails and conversation." - josh barnett, sam faye, john ringor

"The Matchbox, Chicago’s smallest bar (and one of the city’s best) nestled in River West, was sold in late February." - Naomi Waxman

"The environs may be tiny, but the pours are generous at this legendary West Town bar, which clocks in at a cozy 460 square feet. If patrons are lucky enough to snag a seat, most consider it a solid night of watching the bartenders do what they’ve been doing best for the past 25 years — shaking and straining spot-on variations of the classics, from margaritas and gimlets to Manhattans and old fashioneds. Forget too-filled martini glasses here — a mini carafe accompanies every order, ensuring no spills and big-time patron gratitude." - Nicole Schnitzler

"The Matchbox is the smallest bar in the city, and it makes some of the better classic cocktails around. If you roll your eyes when people talk about making friends at bars, come here - you’re in such close quarters that it’s impossible for conversations not to overlap and intersect until you've got a new group of drinking buddies." - Josh Barnett

"Known as Chicago's tiniest bar, the narrow sidecar-esque spot has some of the best deals on some of the best throwback classic cocktails in town. Patrons can order a beer and a shot or a more modern drink, but they often kick themselves for not getting a martini or a Manhattan where the shaker and martini glass are delivered to you and amount to two drinks in one." - Daniel Gerzina, Ashok Selvam