Writer, director and actress Heidi Van Lier won top honors at the 1999 Slamdance Film Festival (an independent-oriented alternative to the concurrent Sundance Festival) for this offbeat comedy about love and romantic fixation. Heather Green (Van Lier) is a journalist with an alternative newspaper in Chicago who is obsessed with her ex-boyfriend, whom she still follows around from time to time. Randy (Joe Kraemer) is in turn obsessed with Heather; a would-be documentary filmmaker, he constantly films her, sometimes without her knowledge. When Heather takes up a challenge from Randy and announces she can seduce the next man she meets, her desperation makes it clear she's had bad luck with men for a very good reason. When Heather finally does meets the man of her dreams, a good-looking attorney named Cliff (Scott Benjaminson), Heather also has an angry and jealous Randy to deal with. Shot mostly in single takes with semi-improvised dialogue, Chi Girl has enough wit and inventiveness to overcome its occasional technical grit, and it features music from the Chicago-based jump blues act The Mighty Blue Kings.
~ Mark Deming, All Movie Guide