The Best of The Second City: Chicago-Style is a laugh-out-loud love letter to the Windy City. Featuring fan-favorite scenes from our archives—written by legendary alumni like Tina Fey, Bill Murray, Catherine O’Hara, Keegan-Michael Key, Stephen Colbert, and more—plus brand-new original material created just for this show. These hilarious songs, unforgettable characters, and iconic sketches are reimagined and brought to life by a ridiculously funny cast of live comedy pros. Whether you’re visiting Chicago or born and raised in Wrigleyville (our deepest condolences), this show is your comedic cheat sheet to all things Chicago.
SUBMIT UPDATES
The Second City Frequently Asked Questions FAQ
The Second City is at 1616 N. Wells Street, Chicago, IL.
Chaos Theory of Everything (6/11/25-1/1/26)
The Best of The Second City: Chicago-Style (6/1/25-11/24/25)
No Grown-Ups Allowed (6/1/25-9/6/25)
Victor Wong Showcase (5/6/25-5/27/25)
This Too Shall Slap (5/1/25-1/25/26)
Clued In: An Invitation to Die For (10/10/24-10/31/24)
She The People (10/5/24-11/23/24)
Ring Lights & Lattes (9/18/24-10/24/24)
Sheila’s Sister and Her Musical Cousins (5/6/23-5/27/23)
Rizz the Season (11/18/25-1/4/26)
Videos
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The Dance of Death
Steppenwolf (1/29 - 3/22) | |
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Rio: A Tribute to Duran Duran
Raue Center For The Arts (1/23 - 1/23) | |
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The Ultimate Cher Show Starring Annika
Raue Center For The Arts (2/7 - 2/7) | |
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By the Way, Meet Vera Stark
GovState Theatre and Performance Studies (4/9 - 4/12) | |
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Winter Dance Party
Raue Center For The Arts (2/20 - 2/20) | |
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Unleash the Beats
Governors State University’s Center for Performing Arts (3/28 - 3/28) | |
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Dine, Laugh, Love- Valetine's Day Comedy Show and Buffet Dinner
BABS Comedy Club (2/14 - 2/14) | |
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2000s Throwback Hip Hop Party With Too Hype Crew and Bobby Afterlife
BaseCamp Pub (3/6 - 3/7) | |
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My Life as a Cowboy
Open Space Arts (1/23 - 2/8) | |
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Holidays a cappella at Chicago a cappella
Chicago A Cappella (10/25 - 8/25) | |
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