The Infinite Wrench
Aug7
Music & 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, August 7th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Devil’s Daughter
Aug7
Music & Comedy

Devil’s Daughter

The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, August 7th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Aug7
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, August 7th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Honk! A Short Form Improv Show
Aug7
Music & Comedy, Theatre & Performing Arts

Honk! A Short Form Improv Show

Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…

Friday, August 7th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Aug7
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, August 7th
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
Aug7
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, August 7th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Aug8
Music & Comedy

Stargazers Adventure Club

Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…

Saturday, August 8th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
The Infinite Wrench
Aug8
Music & 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…

Saturday, August 8th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Aug8
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday, August 8th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Aug8
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday, August 8th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Jack Harlow – The Monica Tour
Aug8
Music & Comedy

Jack Harlow – The Monica Tour

Jack Harlow is scheduled to perform in Chicago on Saturday, August 8, 2026, as part of “The Monica Tour”. This tour supports his recently released,…

Saturday, August 8th
7:30 p.m.10:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Chance The Rapper Live In Concert
Aug8
Music & Comedy

Chance The Rapper Live In Concert

Chance the Rapper is scheduled to perform in Highland Park on Saturday, August 8, 2026, as part of the Ravinia Festival summer lineup. This highly…

Saturday, August 8th
7:30 p.m.10:30 p.m.
Hunter Pavilion At Ravinia
200-201 Ravinia Park Road
Secret Sketch Show
Aug8
Music & Comedy

Secret Sketch Show

Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…

Saturday, August 8th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Aug8
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, August 8th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Wheel of Improv
Aug9
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, August 9th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Hugh Jackman With The Chicago Philharmonic
Aug9
Music & Comedy

Hugh Jackman With The Chicago Philharmonic

Hugh Jackman is scheduled to perform at the Ravinia Festival in Highland Park on Sunday, August 9, 2026. He will be accompanied by the Chicago…

Sunday, August 9th
8:00 p.m.10:00 p.m.
Hunter Pavilion At Ravinia
200-201 Ravinia Park Road
Tuesday Good Show
Aug11
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, August 11th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Brian McKnight & Gladys Knight Live In Concert
Aug11
Music & Comedy

Brian McKnight & Gladys Knight Live In Concert

Brian McKnight and Gladys Knight are scheduled to perform together in Highland Park on Tuesday, August 11, 2026, as part of the Ravinia Festival summer…

Tuesday, August 11th
7:00 p.m.10:00 p.m.
Hunter Pavilion At Ravinia
200-201 Ravinia Park Road
J. Cole – The Fall-Off World Tour
Aug11
Music & Comedy

J. Cole – The Fall-Off World Tour

J. Cole will bring his “The Fall-Off World Tour” to Chicago for a performance at the United Center on Tuesday, August 11, 2026.

Tuesday, August 11th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
Comic Court: Chicago’s #1 Comedy Court Show
Aug11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Comic Court: Chicago’s #1 Comedy Court Show

Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…

Tuesday, August 11th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Jazzin’ at the Shedd
Aug12
Museums, Galleries & Exhibitions, Music & Comedy

Jazzin’ at the Shedd

Live jazz revels at Shedd Aquarium! Join us for the popular midweek  Jazzin’ at the Shedd series with unforgettable evenings of music, mingling and marine life.…

Wednesday, August 12th
5:00 p.m.10:00 p.m.
Shedd Aquarium
1200 S. Lake Shore Dr.
Joe Bonamassa Live In Concert
Aug12
Music & Comedy

Joe Bonamassa Live In Concert

Joe Bonamassa is performing in Highland Park, IL, on Wednesday, August 12, 2026, as part of the Ravinia Festival.

Wednesday, August 12th
7:30 p.m.10:30 p.m.
Hunter Pavilion At Ravinia
200-201 Ravinia Park Road
Hooch & Holler Comedy Show
Aug12
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, August 12th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Aug12
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday, August 12th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.