It wouldn't be fair to start with anyone else but Henry Darger, the big kahuna of the bizarre and Chicago native. He was a reclusive man, fiercely religious who led a humdrum life as a workaday custodian. At night, he wrote and drew absolute tomes of work, one giant story, with four main characters: The Vivian Girls, now forever crystallized in popular culture as a hit indie band. Blah. Anyways, Darger wrote and illustrated crazy adventures from their lives, running away from soldiers and frolicking amongst naked girls with penises. A recreation of his room is free for viewing and open to the public at Intuit: The Center for Outsider and Intuitive Art on Milwaukee Ave., south of Chicago. http://art.org/ They also have a cool exhibit with some crazy folk art needlepoints from the 70's (think satin pools and embroidered bikinis) through the end of the month. Check it out!
Also, stop by the sliver of a bar, the Matchbox, just north of Intuit on Milwaukee, after your visit. It's not called the Matchbox for nothing, it's just a bar and a foot of room behind it, but the gimlets are amazing! House infused gin or vodka, sugar-rimmed, highly alcoholic, and far too delicious. The bartenders give you everything in the shaker, so watch out! However, there are no menus, so you have to ask for the house specials. They also have a fine beer selection and a strange mix of folks. A perfect cap to a Darger viewing.
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