111 West Jackson

Zip to the roof of this 25-story Loop office tower for stunning panoramic views to the south, a bird's eye view of the federal prison's rooftop basketball court, a full, uninterrupted profile of the Willis Tower, and a close-up look at the Chicago Board of Trade Building. The 1961 building revamped its roof deck in 2012, part of a trend toward outdoor amenity spaces for downtown office workers.

A. Epstein & Sons, 1961