Try Chicago's Cherry Circle Room's Ice Cream Cocktails Now

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Across the street from Chicago's sculpture-filled Millennium Park stands a gorgeous circa-1890s Venetian Gothic building, a one-time men's club that has now morphed into the fashionable Chicago Athletic Association hotel. Chocolate doughnuts kick off mornings in the Milk Room, and the Game Room serves pineapple Collins alongside the shuffleboard courts, but evenings end with boozy ice cream cocktails in the Cherry Circle Room.

After, say, steak tartare prepared tableside and halibut heightened by from-scratch Bloody Mary mix, the Old World vibe in the curvy wood space only intensifies with one of these after-dinner drinks, adorably served with straws in retro glass bottles. The drinks, all featuring stellar cordials from California-based Tempus Fugit Spirits and locally made Bobtail vanilla ice cream, pay homage to such postprandial classics as the minty Grasshopper, New Orleans' beloved Brandy Alexander and the more obscure Pink Squirrel, starring almond flavored crème de noyaux.

Paul McGee, beverage director of restaurant group Land and Sea Dept., dreamed up the dessert concoctions as an ode to the "1950's feel of the room," he says. "I would like to think that members of the club and their guests were enjoying Pink Squirrels and Grasshoppers while reading The Wall Street Journal or the sports page back then."

With a setting—and drinks—as seductive as these, they still gladly would.