Life's A Cabernet, Chicago

What was supposed to be a vacation to Napa changed Christopher Libby’s life. Visiting California's thriving vineyards made him realize that life was too short to dislike his career, so he quit his job. He then enrolled in school, became an executive sommelier, and beat Liza Minnelli in a game of Rock, Paper, Scissors to win the right to name his wine shop Life’s A Cabernet. Inside, floor-to-ceiling cubbies highlight Libby's main fare—500 unique bottles of wine—though his shelves also display a collection of 75 craft beers, small-batch scotch and whisky, and handcrafted gin and tequila. In the spirit of wine appreciation, Christopher leads a club through which members receive a bottle of wine each month that he chooses, often a white, red, or bubbly vintage that pairs with the seasons.