alamarcoApologies for the late update. I searched Google and found nothing in the Chicago area. I also went looking around one day and didn't find anything either (went shopping from shop to shop driving around). It was depressing not finding anything at all. I was only in the city though and not the outskirts.
I talked to a friend who has family in the Chicago area and he said there used to be a couple decades ago, but he wasn't sure if they were still around. He said they were in run down areas so he didn't think they did that well and might not still be around.
This was my experience, too. :( Only I did everything by local transit so the adventure was a little painful haha. I just moved to Chicago from the Seattle area (which is anime shop packed), so I was a little spoiled... and disappointed to find that Chicago has no decent bootleg-free anime shops.
There is one shop in chinatown, but as I mentioned, they really only sell bootlegs.