Looks like there is another organization following and questioning surveillance in Chicago - the Lucy Parsons Lab
They have been filing FOIA requests and recieving documents from the police. They are responsible for looking into the cell phone site simulators:
Over the last ten years, over $700,000 has been spent on cell tracking equipment including Harris Corporations's Stingray, KingFish, and AmberJack and Digital Receiver Technologies' DRTBox. The details of cell site simulator purchases is known from work by Freddy Martinez, who first revealed that Chicago police had purchased Stingray devices from Harris corporation and Ali Winston, who revealed that cell site simulators had been first purchased by Chicago police as far back as 2005.
Besides the investigative work, Jennifer Helsby has put together a wonderfully informative site on the state of surveillance in Chicago. Much of this is familiar to this audience, but its the go to starting point for learning about surveillance in Chicago.