The Roof lives up to its name with impressive views of the Chicago skyline from the 27th floor of theWit Hotel. An outdoor lounge lets patrons soak in the sun on warmer days, while an indoor area (complete with fireplace) offers some respite from the brutal winter winds. The stainless steel and gray accents exude industrial cool, but plush lounge chairs and low tables keep the atmosphere light and enjoyable. Guests can listen to the grand piano or spy on the city below with a telescope.