Hilliard Towers Apartments
"Continue West on Cermak and cross State street. On the South side of the street about 100' past the intersection are some concrete barriers. If it's safe, jump the barriers and go straight South on the now-abandoned road. There might be interesting things along this road, take some pix if you see anything. If it's not safe, continue down the block to the National Teacher's Academy and work your way South through their walkways and parking lots. Either way, make your way to the intersection of Federal and W 23rd."
This area is a pretty barren park now but there is a great view of the historic Hilliard Apartments. Built in 1966, the cylinder towers were designed for seniors and the curved towers for low income housing. They were designed by Bertrand Goldberg. He also designed Marina City.