The tiny bar that could. Located at the three-way intersection of Chicago, Ogden and Milwaukee, this one-room tavern is smaller than most people’s studio apartments. But if the crowded confines keep some away, it’s the draw for others. That, and a staff consisting of the best bartenders in the city, pourers who do every drink right even if it takes a couple of extra minutes. And those drinks? Legendary. Whether it’s the gimlet with a sugar rim, a white-chocolate martini (complete with an edible chocolate stirrer) or just a very dry Ketel One martini, up with three olives, the libations at the Matchbox are as topnotch as it gets.
770 North Milwaukee (312)666-9292
Best of Chicago 2002