Chicago comedy spotlight for Monday, August 30-Sunday, September 5, 2021

All shows are in person unless otherwise noted. Please confirm all details. Please also see my 101+ Chicago Comedy Ticket Alerts here. Following is just a sample of all the excellent original comedy happening in Chicago this week.

MONDAY, AUGUST 30

The Chair ONLINE 6:00 p.m. The cast of Netflix’s The Chair: Amanda Peet, Bob Balaban, Holland Taylor, Nana Mensah, Jay Duplass, and Sandra Oh in Conversation with Variety’s Jenelle Riley.

Magic Silly Mondays at The Laugh Factory, 8:00 p.m. Broadcasting live on WGCI. Zach Boog hosts Paul Farahvar, Kellye Howard and more TBA.

TUESDAY, AUGUST 31

The Best of Second City at Second City’s UP Comedy Club, 8:00 p.m.

WEDNESDAY, SEPTEMBER 1

Wednesday After Work at Zanies Chicago, 8:00 p.m. Standup at 8:00 p.m., but doors open at 6:30 p.m. for pre-show drinks and music.

Comedians You Should Know at Timothy O’Toole’s, 7:30 p.m. and 9:00 p.m. Jonah Jurkens hosts Kristen Toomey, Kellye Howard, Joe Kilgallon, Michael Njuguna Robinson.

THURSDAY, SEPTEMBER 2

Tom Dreesen Presents… Standup Comedy: Yesterday, Today, and Tomorrow at Laugh Factory, 1:00 p.m. With Dobie Maxwell. Free, but registration required. An opportunity to hear from two of comedy’s greatest.

Tuxedo Cat Comedy at Beauty Bar, 8:00 p.m. Hosted by Rebecca Fass.

Congrats on Your Success at City Farm Chicago, 8:00 p.m. This acclaimed showcase is outdoors this month and free.

Wisecrackin’ Comedy Game Show at Laugh Factory, 8:00 p.m. Marz Timms in person and Greg Proops streams in from L.A.

FRIDAY, SEPTEMBER 3

Ms. Pat at Zanies, Chicago, 7:00 p.m. Through September 6.

Drink Date Laugh at Laugh Factory, 7:00 p.m. Interactive comedy game show created and hosted by Paul Farahvar. Featuring Sarah Perry, Kyle Scanlan, Andy Fleming, Chastity Washington, Scott Duff and more TBA.

Sarah Squirm at Sleeping Village, 8:00 p.m. Sold out, but I always think it’s worth a call to see if they can fit you in.

SATURDAY, SEPTEMBER 4

Paper Machete at The Green Mill, 3:00 p.m. This legendary variety showcase is back! Early arrival recommended.

She The People at Second City, 8:00 p.m. “Entirely created, designed, and performed by the fearlessly funny women of The Second City!”

SUNDAY, SEPTEMBER 5

Chicago Greek Comedy All Stars at Riddles, Alsip, 7:00 p.m. Chastity Washington (Sigma Gamma Rho), Mark Simmons (Phi Beta Sigma), Aaron Foster (Kappa Alpha Psi), Kadeem Fuller (Alpha Phi Alpha), and LeLe Mason (Delta Sigma Theta). Music provided by DJ B Real (Iota Phi Theta).

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