Yep, pistols are pretty tough.
He has to have a FOID card even to buy ammunition and yes if in the City of Chicago, you need to get a CFP (Chicago Firearms Permit) and then register each gun as you get it.
Out of state must be through a FFL.
It is so much easier to just buy in state - that is what I usually do. You can find deals if you look around - there are classifieds and sales at local gun shops and ranges.
It is not too bad, just wish IL would get on board with the rest of the nation and allow some kind of carry law. I think I'll be dead by the time it is allowed in this wonderful state.
I should move.