Chicago’s Kimpton Gray Hotel is the perfect downtown spot for groups to go when they want to escape. Want to travel back in time to when a martini with lunch was not just accepted, but encouraged and smoking lounges were commonplace? Want to cross the border and explore the culinary adventures of Latin America mixed with Asian influences?  Well, then your dreams have come true at the Kimpton Gray Hotel in Chicago’s Loop. Bonus? Both are available in the same hotel just a quick elevator ride away. 

Vol. 39, named for a trove of vintage encyclopedias found during a renovation, celebrates Chicago’s past with soft lighting, dramatic bookshelves and deep leather sofas. Located in the lobby of the Kimpton Gray Hotel, the law library-inspired bar offers a detailed cocktail menu as well as a refined wine menu of rare, hard-to-find vintages served in high-end stemware. 

Lauren Parton, Vol. 39’s sommelier and bar manager, works hard with Jess Lambert, head bartender, to bring non-mainstream wines to the forefront and make lesser known varieties easy to understand and digest. Their unique signature drinks include the Abeja Blanca is a tequila-based drink mixed with chamomile, and lemon and topped off with fresh honeycomb from a community garden. Beyond Words features a mix of Hendrick’s gin, tropical green tea, and pineapple cardamom foam with a tropical flower garnishing the rim. Both of which this author tasted—you can’t go wrong with either option.

Other highlights include eight different takes on the classic old fashioned and a martini flight offered during happy hour allowing guests to sample all six cocktails.

Tableside food service offers an elegant mix that includes such delights as deviled eggs, a shellfish tower and a pork belly pastrami panini. For a more elevated experience, guests can sample caviar, cheese, charcuterie and champagne all wheeled over on a golden cart. Everything from the service to the ambience at Vol. 39 pays homage to Chicago’s storied and honorable past.

Next up is the Boleo Rooftop. Take your group upstairs and be instantly transported to a tropical paradise. Featuring an open roof, exotic flowers and greenery, and white linen furniture, Boleo exudes Latin American cocktail bar culture. 15 floors above the street, chef Alexis Hernandez has fashioned a menu of snackable ceviches, anticuchos and other small plates with a contemporary touch, all inspired by Peruvian street food with Asian influences. Head Bartender Jess Lambert has crafted a cocktail menu all her own with offerings so dramatically different from Vol. 39, you will forget you’re even in the same hotel. And, even if the weather is bad, your group can still check out the rooftop—a retractable roof means your safe in all weather conditions. If you stay late enough, a DJ will hit the dance floor, elevating the energy of the space. 

Groups can rent out Ezperanza—a smaller part of the rooftop—for a more intimate dining experience or the entire space for a group of 250. With a retractable roof, live music and a name that describes an Argentinian tango move, Boleo is guaranteed to show guests a good time. 

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