The Tasting Room makes the short list of nightspots where Chicagoans take guests they want to impress. This two-story wine bar has a casual, loft-chic look and sweeping skyline views. More than 100 wines are poured by the glass or flight, and more than 300 by the bottle. Cheese, caviar, and other light bites are the perfect complement. If you love the vintage you taste here, buy a bottle to take home at the adjacent wine shop, Randolph Wine Cellars.