This Week Downtown: Sara Bareilles, Operation Mincemeat, Bill Burr

Your week-ahead guide to Downtown — five picks worth planning around, from Sara Bareilles at The Chicago Theatre to a Tony-winning musical and Bill Burr.

By Raj Singh · Published September 27, 2026.

SUNDAY, SEPTEMBER 27

Sara Bareilles: Good Grief Tour @ The Chicago Theatre

Sara Bareilles plays The Chicago Theatre at 8 PM, touring behind Good Grief — her seventh studio album and first release in seven years.

Jay Washington at The Comedy Bar

Stand-up Jay Washington — a former wrestler turned comic with credits on the Netflix Is A Joke Festival and HBO's Euphoria — headlines The Comedy Bar at 6:30 PM. Tickets run $25–$35.

TUESDAY, SEPTEMBER 29

Operation Mincemeat: A New Musical @ CIBC Theatre

The Olivier Award winner for Best New Musical and a 2025 Tony winner, Operation Mincemeat lands at the CIBC Theatre this week. Set in 1943, it spins the improbable true WWII tale of a corpse, a fake love letter, and Ian Fleming into a fast, funny musical.

THURSDAY, OCTOBER 1

Issa Rae Chicago: Insecure The 10th Anniversary Tour @ The Chicago Theatre

Issa Rae brings Insecure: The 10th Anniversary Tour to The Chicago Theatre at 8 PM — a retrospective marking a decade since the HBO series premiered, with creator-star Issa Rae joined by showrunner Prentice Penny for an evening of conversation.

SATURDAY, OCTOBER 3

Bill Burr Live @ The Chicago Theatre

Comedian Bill Burr closes out the week at The Chicago Theatre with a 10 PM show, per the do312 listing.

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