If you're in the northern burbs, I'd suggest talking to Carlo:
http://carlomastertailor.com/
He's old school from Portugal and did quite a bit of work for me when I lived in the area. While I never had him make a suit for me, his custom shirts were spectacular and very reasonably priced ($125). Block out some time on the schedule if you go visit him - he loves to talk about his trade with customers who actually appreciate the craft.
If you're looking for an afternoon full of conversation, ask him about his apprenticeship. He once spent 2 hours walking me through the finer points of making a buttonhole.