Hitch*Cocktails
Sep25
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, September 25th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Sep26
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, September 26th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
WingOut Chicago 2026
Sep26
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation

WingOut Chicago 2026

WingOut Chicago | Sept 26-27 | Gallagher Way • Chicago Join us at Gallagher Way in Wrigleyville for Chicago’s most mouth-watering outdoor event of the…

Saturday, September 26th
11:30 a.m.9:00 p.m.
Gallagher Way
3635 North Clark Street
The Infinite Wrench
Sep26
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, September 26th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Bassem Youssef – The Belly of the Beast Tour
Sep26
Music & Comedy

Bassem Youssef – The Belly of the Beast Tour

Bassem Youssef is scheduled to perform in Chicago on Saturday, September 26, 2026, as part of his “The Belly of the Beast Tour”.

Saturday, September 26th
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Baby Wants Candy! The Original Completely Improvised Musical
Sep26
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, September 26th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Sep26
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, September 26th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Top Gun: Maverick In Concert
Sep26
Music & Comedy

Top Gun: Maverick In Concert

Top Gun: Maverick was nominated for six Academy Awards® including Best Picture and Best Original Song, winning Best Sound. After more than 30 years of…

Saturday, September 26th
7:30 p.m.9:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Juanes: World Tour
Sep26
Music & Comedy

Juanes: World Tour

Juanes is scheduled to perform at the Rosemont Theatre in Rosemont, Illinois, on Saturday, September 26, 2026. This performance is part of his newly announced…

Saturday, September 26th
8:00 p.m.11:00 p.m.
Rosemont Theatre
Foster The People – Good Mourning Sunshine Tour
Sep26
Music & Comedy

Foster The People – Good Mourning Sunshine Tour

Foster The People will bring their “Good Mourning Sunshine Tour” to the Huntington Bank Pavilion at Northerly Island on Saturday, September 26, 2026. Special Guest:…

Saturday, September 26th
8:00 p.m.11:00 p.m.
Secret Sketch Show
Sep26
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, September 26th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Sep26
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, September 26th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
WingOut Chicago 2026
Sep27
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation

WingOut Chicago 2026

WingOut Chicago | Sept 26-27 | Gallagher Way • Chicago Join us at Gallagher Way in Wrigleyville for Chicago’s most mouth-watering outdoor event of the…

Sunday, September 27th
11:30 a.m.9:00 p.m.
Gallagher Way
3635 North Clark Street
Dying Fetus & Sanguisugabogg – 2026 Tour
Sep27
Music & Comedy

Dying Fetus & Sanguisugabogg – 2026 Tour

Dying Fetus and Sanguisugabogg are bringing their co-headlining tour to the House of Blues Chicago on Sunday, September 27, 2026. Supporting Acts: Crowbar, Left to…

Sunday, September 27th
5:30 p.m.11:00 p.m.
Malarkey Comedy Expo League
Sep27
Music & Comedy, Theatre & Performing Arts

Malarkey Comedy Expo League

Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…

Sunday, September 27th
6:00 p.m.7:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
Bryson Tiller – The Neo Trapsoul Tour
Sep27
Music & Comedy

Bryson Tiller – The Neo Trapsoul Tour

Bryson Tiller is performing live in Tinley Park on Sunday, September 27, 2026, as a headlining stop on “The Neo Trapsoul Tour”.

Sunday, September 27th
7:30 p.m.10:30 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
Improvised DCOM
Sep27
Music & Comedy, Theatre & Performing Arts

Improvised 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 with…

Sunday, September 27th
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Cavetown – Running With Scissors Tour
Sep27
Music & Comedy

Cavetown – Running With Scissors Tour

Cavetown is bringing the Running With Scissors Tour to The Salt Shed in Chicago on Sunday, September 27, 2026.

Sunday, September 27th
8:00 p.m.11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Sara Bareilles – Good Grief Tour
Sep27
Music & Comedy

Sara Bareilles – Good Grief Tour

Sara Bareilles will perform live at The Chicago Theatre on Sunday, September 27, 2026, as part of her newly announced “The Good Grief Tour”. The…

Sunday, September 27th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
MICO – Running From A Feeling Tour
Sep29
Music & Comedy

MICO – Running From A Feeling Tour

The pop-punk and alternative artist MICO is scheduled to perform live in Chicago, Illinois on Tuesday, September 29, 2026. The performance is part of his…

Tuesday, September 29th
6:00 p.m.9:00 p.m.
Tuesday Good Show
Sep29
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, September 29th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Arlo Parks – Desire Tour
Sep29
Music & Comedy

Arlo Parks – Desire Tour

Arlo Parks is bringing her Desire Tour to Chicago on Tuesday, September 29, 2026, at the historic Thalia Hall. The tour follows the release of…

Tuesday, September 29th
8:00 p.m.11:00 p.m.
Thalia Hall
"1621 Central Ave, Suite 330 Cheyenne, WY 82001"
Johnny Blue Skies & The Dark Clouds – Mutiny for the Masses 2026 Tour
Sep29
Music & Comedy

Johnny Blue Skies & The Dark Clouds – Mutiny for the Masses 2026 Tour

Johnny Blue Skies (the pseudonym for Sturgill Simpson) and his band The Dark Clouds are scheduled to perform at the United Center in Chicago on…

Tuesday, September 29th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
Lambrini Girls – 2026 World Tour
Sep29
Music & Comedy

Lambrini Girls – 2026 World Tour

Lambrini Girls are scheduled to perform at the Vic Theatre in Chicago on Tuesday, September 29, 2026. with special guests Big Special and Big Girl.

Tuesday, September 29th
8:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield