I have searched and searched but have not been able to find anywhere in the ChicagoLand area that provides topless or naked haircuts.  Any help would be appreciated.

try this lady. She is an escort who also does hair cuts. Never tried her hair cut
If you can tolerate her incessent talking and ok with not so hot looks she will get the job done I think. your request is unique so pointing you to a possibility. Don't take it as a recommendation. She has a great butt though.