Theatre & Performing Arts
Issa Rae – Chicago – Insecure: The 10th Anniversary Tour October 1, 2026
Writer, producer and actress Issa Rae is bringing Insecure: The 10th Anniversary Tour to Chicago on Thursday, October 1, 2026, for a live celebration at The Chicago Theatre.
The Production: Celebrating a decade since the premiere of her groundbreaking HBO series, creator and star Issa Rae is hitting the road alongside showrunner Prentice Penny. The retrospective tour features intimate conversations, behind-the-scenes secrets, and a retrospective look at the show’s cultural impact.
The Cast: In addition to Issa and Prentice, select dates feature key cast members including Yvonne Orji, Jay Ellis, and Natasha Rothwell (cast appearances are subject to availability).
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Loop
This city center is home to some of Chicago’s most iconic attractions and architecture.
Learn more about the area
Neighborhood
Loop
This city center is home to some of Chicago’s most iconic attractions and architecture.
