1. Watch a movie on a Whole Foods roof
The giant Whole Foods in Lincoln Park is doing a run of weekly female-centric movie screenings on its roof. The series is curated by comedian Whitney Cummings, and this week's showing will feature the cult classic Ghost World. Regardless of whether you're into the film, everyone loves a good roof during the summer. (Whole Foods Market Lincoln Park, 1550 N Kingsbury St, 7:30pm. Free)
2. Get weird at the Old Town School of Folk
The alt-folk oddball Will Oldham, more regularly known as Bonnie "Prince" Billy, is heading to the Lincoln Square location of the Old Town School of Folk Music for a show with labelmates Faun Fables. Oldham released a new album last year, Singer's Grave a Sea of Tongues, but he's probably already cooked up another batch of tunes. Expect to hear a mix of old favorites and fresh songs from the fabulous songwriter. (Old Town School of Folk Music, 4544 N Lincoln Ave, 10pm. $28–$30)
3. Catch Stick Fly before its run ends
Lydia R. Diamond's 2006 play Stick Fly is in the last week of its run at Windy City Playhouse. The play made its Broadway debut more than three years ago, and it's still relevant as ever. Set in Martha’s Vineyard at the ancestral summer home of a wealthy African-American family, the play’s characters challenge each other on matters of race as it relates to privilege and class. (Windy City Playhouse, 3014 W Irving Park Rd, 7:30pm. $20–$45)