1. Chance Encounter
West Chatham’s own Chance the Rapper (above) brings his bars to Ravinia. Get ready to blow him cocoa butter kisses from the lawn. Aug. 8. ravinia.org
2. Ex-Xers
Four decades past their heyday in the band X, punk-rock royalty John Doe and Exene Cervenka show their chops with an acoustic set at the Old Town School of Folk Music. Aug. 8. oldtownschool.org
3. Holy Hatter
Celebrate the world’s most famous White Sox fan at this promotional night at Rate Field. Everyone — yes, even Reds fans — gets a dope Pope Leo hat. Aug. 11. mlb.com/whitesox
4. Too Important Not to Joke About
Never intimidated by a tough topic, Tony- and Emmy-winning comedian Alex Edelman mulls the Israel-Palestine conflict in his new one-man show, What Are You Going to Do. Aug. 12–16. steppenwolf.org
5. By the Blue Purple Yellow Red Water
Kokandy revives Sondheim’s Seurat-inspired musical masterpiece Sunday in the Park With George, starring Kevin Webb (the company’s former Sweeney). Aug. 13–Nov. 1. kokandyproductions.com
6. Comeback Blitz
The beloved Midwest emo band American Football, formed in Champaign-Urbana in the late ’90s, returns to hypnotize crowds. Aug. 14. saltshedchicago.com
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7. Smoke Screen
The audacious thriller Sinners — starring Oscar winner Michael B. Jordan as twins Smoke and Stack, plus a cameo by Buddy Guy — closes out Millennium Park’s free summer film series. Aug. 18. chicago.gov
8. Lords of the Dance
For its 35th anniversary, Dance for Life features pros from Hubbard Street, Trinity Irish Dance, Ensemble Español, and more. Randy Duncan choreographs the world premiere finale. Aug. 22. cdhf.org/danceforlife
9. Clique Shtick
The power-pop musical of Tina Fey’s Mean Girls comes to Aurora. Jeff winner Elizabeth Stenholt plays Cady, vying against the titular trio. Aug. 26–Oct. 11. paramountaurora.com
10. Standup Guy
Comedian Kasaun Wilson’s crusade for a four-day workweek is a primo bit. The staff writer for Jon Stewart brings his full set to the Lincoln Lodge. Aug. 30. thelincolnlodge.com