4. I|O Urban Roofscape
Meet your new outdoor playground: 15,000 square feet of plush lounges, leather banquets, chrome tables, and a retractable glass ceiling with views of the top of the skyline. A killer selection of kitchen cocktails includes something called the Chef’s Margarita and a version of the classic gin and tonic made with Chartreuse.
127 W. Huron St., River North (312-649-2000).