1 Vonnegut on Again

Rogers Park’s Lifeline Theatre, which recently marked 40 years of staging original literary adaptations, revisits a favorite: Second City and Cardiff Giant alum John Hildreth’s 2002 version of Kurt Vonnegut’s satirical novel Cat’s Cradle. Sept. 1–Oct. 22. lifelinetheatre.com

2 Arts Encounter

While Millennium Park as a whole will celebrate its 20th anniversary next summer, the Harris Theater for Music and Dance throws itself a birthday party this month. The all-day Harris Fest brings together more than a dozen troupes that have called the theater home in its first two decades. Sept. 9. harristheaterchicago.org

3 Words on the Street

If the book fair was your most anticipated event of the school year, then the Printers Row Lit Fest is for you, with author talks and bookseller booths stretching for five blocks. This year’s event is headlined by Robert Samuels and Toluse Olorunnipa, authors of the Pulitzer Prize–winning His Name Is George Floyd. Sept. 9–10. printersrowlitfest.org

4 Latin Light

The Colombian reggaetón artist Karol G became the first woman to top the Billboard charts with a Spanish-language album when Mañana Será Bonito debuted at No. 1 in March. Now she joins the stadium concert ranks, playing Soldier Field. Sept. 15. ticketmaster.com

5 Roll With Funches

Soft-spoken comedian Ron Funches, known for his voice work in animated projects including the Trolls series, grew up in Woodlawn before moving to Oregon as a teenager. He returns for two nights of standup at the Den Theatre. Sept. 15–16. thedentheatre.com

6 ¡Viva Mexico!

The Mexican Independence Day Parade draws 400,000 spectators to 26th Street in Little Village. This year’s edition celebrates the diversity of Mexican heritage, with groups representing each of the country’s 32 states. Sept. 16. littlevillagechamber.org

7 Pearl’s Wisdom

The Goodman opens its fall season with the Chicago premiere of The Nacirema Society, a comedy by the prolific Black playwright Pearl Cleage. Several other theaters across the city are staging concurrent productions or readings of Cleage’s works. Sept. 16–Oct. 15. goodmantheatre.org

8 Ballet Superstar

Seven prominent ballet companies from across the country come together for the Arpino Chicago Centennial Celebration, marking the 100th birthday of the late choreographer and Joffrey Ballet cofounder Gerald Arpino. Sept. 23–24. auditoriumtheatre.org

9 All That Jazz

Hear 35 artists and groups representing the breadth of the genre at the Hyde Park Jazz Festival, now in its 17th year. It’s all free, though a $10 donation is encouraged. Sept. 23–24. hydeparkjazzfestival.org

10 Big Band

The playful New Orleans funk group Tank and the Bangas joins the Chicago Philharmonic Orchestra for an evening of symphonic soul at the Auditorium Theatre. Sept. 30. chicagophilharmonic.org