1. Open since May, Roof occupies the 27th floor of the Wit Hotel. The 7,000-square-foot restaurant pairs small plates with gourmet cocktails, and opens onto a patio with room for 150. The outdoor space, open year-round, offers multiple fire pits, a communal table for 18, and its own bar.
2. In May, Trump International Hotel & Towers opened Terrace at Trump, a swank addition to its 16th-floor restaurant, Sixteen. Overlooking Lake Michigan and the Wrigley clock tower, the space serves cocktails with nautical names and a seasonal menu from chef Frank Brunacci. The entire terrace can host receptions for 150, or a semiprivate area accommodates 100.
3. Perched on top of River North’s Dana Hotel and Spa, Vertigo Sky Lounge opened in October 2008. The venue, which specializes in sushi and Vietnamese sandwiches, offers a 1,000-square-foot year-round patio. Equipped with a crystal-filled fire pit, the space can host receptions for 65.
4. Open since May, the West Loop’s Market has a 4,000-square-foot rooftop lounge. Decked with seven cabanas, the terrace overlooks the city skyline and can seat 200 guests. With indoor reception space for 250, the restaurant offers a menu of whimsically presented American fare such as mac-and-cheese muffins served in picnic baskets.
