Located on the second floor of the Kimpton Gray Hotel, Vol. 39 has an ambiance reminiscent of the 1960s, from décor to menu. Named after the trove of antique encyclopedias that don the walls, the bar’s dim lighting and tufted leather couches pay homage to the past. And with offerings like martini flights and caviar from silver-gilded carts, the lounge emulates opulence from its post in the Loop. Beyond caviar, the elevated, modern fare is limited, mainly focusing on small plates such as oysters, foie gras, and bone marrow, and of course artisanal cheese and charcuterie selections. The beverage menu is the star, with six variations on both old fashioneds and martinis, a collection of classic cocktails (sazeracs, negroni, sours, and Collins included), their own new and nuanced cocktail visions. Explore the midcentury cocktail menu, or enjoy imbibing from their vast list of wine, beer, rare spirits, and small-batch Champagne (for the caviar, of course).