Never heard of the Raffaello Hotel? Just hope nobody else has either so you can snag a seat at this new 18th-floor rooftop bar overlooking the lake and Gold Coast before the hordes invade. Banquette seating lines the glass-walled perimeter of the 2,000-square-foot space, and lounge chairs circle two fire pits. Rather keep warm inside? Step through the enormous arched doorway to the cavernous main bar, which has 20-foot-high vaulted ceilings, cozy alcoves with an antique fireplace and two bars to grab one of the six to eight seasonally rotating cocktails, which focus on Scotch, whiskey and bourbon. Small plates from the hotel’s Italian restaurant, Pelago, are available inside and out.
201 E Delaware Pl, 18th floor (312-924-2531).