As you enter the stylish Raffaello hotel, your date may begin to wonder what you have in store for the evening. The secret is revealed as the elevators open to the 18th floor, where you’ve booked a table for two at Drumbar just in time for sunset. This sky-high cocktail spot is the perfect place to impress your special someone with a drink and a view, so take your seats on the patio and get ready for an evening to remember. They’re serious about mixology here, so go beyond your standard G&T and pick something off the deliciously creative cocktail list. The Chicago cocktail is perfect for purists, its sultry blend of cognac and orange curacao enlivened by a splash of bubbly prosecco. But your sweetheart might resemble the Pretty Mayhem, with tequila, rabarbaro (something like rhubarb), strawberry, lemon, cinnamon, and bitters at once asserting themselves and complementing the other flavors. Even the ice in the drinks is fancy, be it a perfect frozen orb or massive, flavor-infused, slow-melt cubes that keep your drink tasting perfect to the last sip. The terrace is mostly protected from the wind, but if you do feel a chill once the sun slips below the horizon, head inside and cuddle up on the cushy, curved leather couches in front of the fireplace. It’s about the coziest spot in town to share a nightcap with your special someone.