there are flight schools at Chicago Executive (PWK) not sure if Palwaukee flyers is the same as Windy City flyers but I have friends that work there and love it. Theres a couple of flight schools at MDW but they are not very big operations (1-2 aircraft) then Dupage (DPA) has American Flyers and Illinois
Aviation not sure about either's hiring situation. Then there is Clow (1C5) A&M aviation, they're not hiring. Aurora (ARR) not sure but check it out. and Louis (JOT) Louis University is there with a flight program so they pull from they're students but you might want to check it out. [note: the last three airports area all an hour drive outside of downtown chicago in the west and southwest suburbs.]