Weird Al’ Yankovic – The Bigger and Weirder 2026 Tour
Jun27
Music & Comedy

Weird Al’ Yankovic – The Bigger and Weirder 2026 Tour

Weird Al brings his legendary full-production multimedia comedy rock show back to the concert stage with the BIGGER & WEIRDER 2026 Tour, playing his iconic…

Saturday, June 27th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
Josh Groban Live In Chicago – Gems Tour 2026
Jun27
Music & Comedy

Josh Groban Live In Chicago – Gems Tour 2026

Multi-platinum vocalist Josh Groban/w special guest Jennifer Hudson will perform live at Rosemont‘s Allstate Arena on June 27, 2026.

Saturday, June 27th
8:00 p.m.11:00 p.m.
Allstate Arena
6920 Mannheim Road
Secret Sketch Show
Jun27
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, June 27th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Jun27
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, June 27th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Wheel of Improv
Jun28
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, June 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Madison Beer – Locket Tour 2026
Jun29
Music & Comedy

Madison Beer – Locket Tour 2026

Pop artist Madison Beer will perform in Chicago at the Aragon Ballroom on Monday, June 29, 2026, at 6:30 PM as part of the The…

Monday, June 29th
6:30 p.m.10:00 p.m.
Alex Warren: Little Orphan Alex Live
Jun29
Music & Comedy

Alex Warren: Little Orphan Alex Live

Alex Warren is bringing Little Orphan Alex Live to Chicago’s United Center on June 29!

Monday, June 29th
7:30 p.m.10:30 p.m.
United Center
1901 W Madison St,
Tuesday Good Show
Jun30
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, June 30th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Hooch & Holler Comedy Show
Jul1
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, July 1st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Infinite Wrench
Jul3
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, July 3rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Louis Tomlinson – How Did We Get Here? World Tour
Jul3
Music & Comedy

Louis Tomlinson – How Did We Get Here? World Tour

Louis Tomlinson is scheduled to perform in Rosemont, IL, on Friday, July 3, 2026, at the Allstate Arena. The show is part of his “How…

Friday, July 3rd
7:00 p.m.10:00 p.m.
Allstate Arena
6920 Mannheim Road
Devil’s Daughter
Jul3
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, July 3rd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Jul3
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, July 3rd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
Jul3
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, July 3rd
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
Jul3
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, July 3rd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Jul4
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, July 4th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Jul4
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, July 4th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Jul4
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, July 4th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Secret Sketch Show
Jul4
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, July 4th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Jul4
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, July 4th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
HighQ
Jul5
Music & Comedy, Theatre & Performing Arts

HighQ

Is it a cannabis-themed game show or an uproarious, electively interactive live theatrical experience? Why can’t it be both? HighQ is an uplifting blend of…

Sunday, July 5th
6:00 p.m.7:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Wheel of Improv
Jul5
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, July 5th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
Jul7
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, July 7th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Evanescence Live In Chicago – 2026 World Tour
Jul8
Music & Comedy

Evanescence Live In Chicago – 2026 World Tour

Grammy Award-winning band Evanescence /w special guests Spiritbox & Nova Twins will perform live at Credit Union 1 Amphitheatre on July 8, 2026.

Wednesday, July 8th
6:30 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave