Bizarre Chicago, run by Bucktown-Wicker Park resident Gordon Meyer, offers unique and entertaining neighborhood walking tours. The top-rated and popular small-group tours focus on forgotten history, unexplained mysteries, and ghost stories.
Quimby's is definitely a specialist bookstore. As they put it, the offer "aberrant periodicals, unusual publications, saucy comic books, and assorted fancies." All that, and it doesn't even include the 'zines. (Self-published magazines that cater to any interest you can imagine -- and probably several you can't.)