Eno Wine RoomStreeterville | Website
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You’ll find a tasty trifecta of wine, cheese and chocolate at this Loop wine bar in the chic lobby of the Fairmont Hotel (Its sister spot is at the Intercontinental.) Vino is available by the bottle, glass or as part of a themed flight, while charcuterie and artisanal cheese plates are available accompanied by fruit spreads and nuts. Approachable servers specialize in tableside education, and they also teach a series of classes for those who want to brush up on their knowledge of world-class wines (The list has more than 300). For those with a sweet tooth, locally crafted truffles round will out the experience.