Kennedy Rooftop

Unlike the expressway by the same name, Chicagoans will actually want to hang out at the Kennedy Rooftop, located on top of the Hyatt Place Chicago in Wicker Park. Here, guests are afforded unobstructed skyline views that stretch from the John Hancock to the Willis Tower in addition to 7,500 square feet to roam. A lineup of craft cocktails pays homage to past presidents, like Reagan’s Orange Blossom with botanical vodka, orange juice, lemon, orange bitters and club soda. When your eyes aren't fixed on the knockout views, try your hand at life-size Jenga or warm up by the outdoor firepits.