Whiskey Blue

Other than their crisp uniforms, it's hard to tell the difference between the attractive, slick waitstaff and the beautiful people milling about this well-stocked watering hole right off the Living Room (aka the lobby) of the W Chicago City Center. Owned by Cindy Crawford's husband Rande Gerber, it's packed on weeknights with fashion-forward out-of-towners and even more style-conscious Chicagoans, but sparse on the weekends when downtown clears out and other club options are more viable.