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Music & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday, September 3rd
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMusic & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Thursday, September 4th
6:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy, Tours & Attractions
Randy Houser Live
Randy Houser is bringing his signature powerhouse vocals to an exclusive, one-of-a-kind performance on Lake Michigan with City Cruises Live. Trading the big stage for…
Thursday, September 4th
6:00 p.m. – 10:00 p.m.City Cruises Chicago – Navy Pier
600 E Grand AveMusic & Comedy, Theatre & Performing Arts
Love Is Improvised
An improvised take on a hit reality-TV show that dares to ask… is love truly improvised? A cast of 10 improvisers will embark on a…
Thursday, September 4th
7:00 p.m. – 8:00 p.m.The Second City
230 W North Ave., 2nd FloorMusic & Comedy, Tours & Attractions
Randy Houser Live
Randy Houser is bringing his signature powerhouse vocals to an exclusive, one-of-a-kind performance on Lake Michigan with City Cruises Live. Trading the big stage for…
Thursday, September 4th
7:00 p.m. – 10:00 p.m.Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United StatesMusic & Comedy, Theatre & Performing Arts
Olympus Has Fallen (And It Can’t Get Up)
Olympus Has Fallen (And it Can’t Get Up) is a sketchy retelling of your favorite Greek myths. As educational as it is explicit, this hour-long…
Thursday, September 4th
7:30 p.m. – 8:30 p.m.The De Matt Theater at The Second City
230 W North AveMusic & Comedy
The Music of David Sanborn
On May 12th, we commemorated the first anniversary of the passing of the legendary alto saxophonist David Sanborn. To honor his immense contribution to music,…
Thursday, September 4th
7:30 p.m. – 9:00 p.m.city winery chicago
1200 W. Randolph StreetMusic & Comedy, Theatre & Performing Arts
BULL
This original comedic play follows unproven jokesters Scott and Bryce, who find themselves at the pinnacle of the basketball world — the 1996 Chicago Bulls.…
Thursday, September 4th
7:30 p.m. – 9:00 p.m.The Annoyance Theatre
851 W. Belmont Ave.Music & Comedy
OhJay Lamont
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…
Thursday, September 4th
7:30 p.m. – 9:00 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy, Theatre & Performing Arts
Hot People Island
Hot People Island is a world premiere original comedy by Deana Velandra. In this play, a popular television network will take eight lucky certified Hot…
Music & Comedy, Theatre & Performing Arts
Improvsed DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…
Thursday, September 4th
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
Sketch Playlist
Sketch Playlist is a weekly sketch show on Thursdays at 9:30pm at iO Theater (1501 N Kingsbury Street, Chicago 60642) that will feature brand-new material…
Thursday, September 4th
9:30 p.m. – 10:30 p.m.iO Theater
1501 N. Kingsbury St.Music & Comedy
First Friday Music Series
Join us for the First Friday Music Series, an evening of live music that will take place on Sheridan Rd. between Devon and Pratt. Enjoy…
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Friday, September 5th
6:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Mandala Makers Festival
Mandala Performing Arts is proud to announce the 7th annual Mandala Makers Festival, a three-day celebration that provides a platform for emerging South Asian performing…
Friday, September 5th
6:00 p.m. – 11:30 p.m.Athenaeum Center for Thought & Culture
2936 N Southport AveMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Friday, September 5th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy
D’Lai at The Comedy Bar
D’Lai is one of the nations most sought after comics. He has appeared on HBO’s Def Comedy Jam, Showtime, BET’s ComicView, and Kevin Hart’s Laugh…
Music & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Friday, September 5th
7:00 p.m. – 8:30 p.m.Malarkey Comedy
1501 N. Kingsbury St.Music & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Friday, September 5th
7:00 p.m. – 8:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy
Chris Distefano Live
Chris Distefano will perform at The Chicago Theatre on September 5.
Friday, September 5th
7:00 p.m. – 9:00 p.m.The Chicago Theatre
175 N. StateMusic & Comedy, Theatre & Performing Arts
Improvised Shakespeare
Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare
Music & Comedy, Theatre & Performing Arts
Hot People Island
Hot People Island is a world premiere original comedy by Deana Velandra. In this play, a popular television network will take eight lucky certified Hot…
Music & Comedy
Dua Lipa – Radical Optimism Tour
Dua Lipa is bringing the Radical Optimism Tour to United Center on September 5 & 6, 2025!
Music & Comedy
LE SSERAFIM – EASY CRAZY HOT TOUR
K-pop sensation LE SSERAFIM will perform live at Wintrust Arena on Sep. 5, 2025.
Friday, September 5th
7:30 p.m. – 10:30 p.m.

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