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I went to Dave's Records, which I think was on Clark. The owner (Dave, I presume) was pretty nice and I found a couple of good records there. My general impression of Chicago record stores were that they were expensive, even compared to the ones I've frequented in NYC and Boston. The Reckless Records chain was pretty meh.... Probably about 80% of their stock was new stuff. That all said, I probably only hit about half the places I could have.
Quimbys books was pretty cool. I got a great Fantagraphics book about 30s-40s superhero comics. Myopic Books in that neighborhood was pretty good too... It had that used bookstore smell.