Here's a printable "tour" itinerary for the Brown Line, which as a bonus is also almost fully accessible now.
http://pn.psychiatryonline.org/cgi/c.../full/37/15/22
(interestingly, I was searching for a similar, if more detailed, itinerary written for another APA: the American [Urban] Planners Association, but this will do.)

There are hundreds of theater choices beyond the Loop; check Reader or Time Out listings for reviews. Indeed, many would be just off the Brown Line in Lakeview.