Not a Chicago guy but what a do is avoid horizontal runs much as possible. When I had to go horizontal, I'd go through wish a piece of scrap wood that was cut to the height I am going to run horizontally. I'd then go through with a circular saw and make a cut ONG mark and about an inch higher the cut would be just deep enough for the conduit. I'd then go through with my hammer and pop out the piece of wood between the cuts. I would use nail plates to secure the conduit in place.
It sounds labor intensive but if done right, it's quicker then a hole hog and don't have to wrestle the comduit in place.
