try seeing something at Steppenwolf Theatre Co. (Home of Tracy Letts, winner of many Tony's in 2008 for August: Osage County, which premiered here...also home to his Superior Donuts, which opened last summer and is transferring to Broadway this fall!)
Right now, "UP" by Bridget Carpenter is playing, and has gotten very good reviews. I have friends who have seen it and loved it (quirky but deep they say):
http://www.steppenwolf.org/boxoffice/productions/index.aspx?id=459 Also, check out "BLACKBIRD", playing at Victory Gardens. The two-person cast stars CSI-star William Petersen...it's a story about a man and his confrontation with a former lover who was underage when they were together. It's gotten rave reviews, but ends August 9th.
http://victorygardens.org/content/node/614 Last, try to get tickets to "THE HISTORY BOYS" at TimeLine Theater. I believe it's already extended 3 times because of the sold-out audiences and popularity. It's also gotten rave reviews, and is I think one of the hottest tickets right now.
http://www.timelinetheatre.com/history_boys/index.htm Hope these give you some ideas, have fun here!