I guess they don't expect anyone to notice there are no palm trees in Chicago. They are targeting churches, schools as well as courthouses where people are trying to go through the process becoming citizens. Guess they are easier to scoop up than the criminals. And food delivery guys. Not sure if he fled before completing the delivery.

https://www.thedailybeast.com/donald-trump-and-white-house-busted-using-florida-dhs-palm-tree-footage-to-show-chaos-in-chicago/

https://www.bing.com/videos/riverview/relatedvideo?q=food%20delivery%20guy%20escaping%20from%20ICE&mid=C3E270D45F61F2572227C3E270D45F61F2572227&ajaxhist=0