Legend has it that on December 5, 1933—the day that Prohibition ended—the Zebra Lounge showed Chicago its stripes for the first time. Fittingly, one must pass under the Canterbury Courts’ black-and-white awning to get to this intimate piano bar, where mustard and mauve-painted walls give way to a hung zebra pelt, framed pictures, and zebra-striped lamps. Even the bartenders match the décor, since they often sport black pants and white socks as they sling drinks and play armchair therapist. In-the-know patrons arrive early to sink into leather booths as pianists tap out songs by Frank Sinatra and Neil Diamond, among others. Later on in the night, the cozy, pint-sized joint fills up with a diverse crowd that leaves the pretension at the door and ranges from suit-sporting old-timers to reveling college students.
From behind the mirror-lined bar, the staff pours martinis, fills wooden bowls with zesty snack mix, and turns away predatory lions lured by the bar’s sign. Zebra Lounge is many things; as much a chameleon as it is a zebra. It’s a hideaway to those that want it to be one, and place to have great conversation for those looking for one.