Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Iron & Wine Live In Chicago
Start: 2026-05-06T20:00:00-05:00
End: 2026-05-06T23:00:00-05:00
Location: Thalia Hall

Check out what's happening all around Chicago.

May 1, 2026: May1
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.…
Lincoln Park
Event details
Friday, May 1st
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
May1
Music & Comedy, Theatre & Performing Arts
Missed Call Sketch Comedy Show
Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!
Lakeview
Event details
Friday, May 1st
8:00 p.m. – 9:00 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May1
Music & Comedy
Demi Lovato Live at United Center – It’s Not That Deep Tour 2026
Award-winning diva Demi Lovato brings her powerhouse voice and fearless stage presence to Chicago on May 1, 2026, for a one-night-only performance at the United…
West Loop
Event details
Friday, May 1st
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,
May1
Music & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…
Event details
Friday, May 1st
8:00 p.m. – 11:00 p.m.
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The Vic Theatre
3145 N. Sheffield
May1
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…
Event details
Friday, May 1st
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,
May1
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…
Lakeview
Event details
Friday, May 1st
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May 2, 2026: May2
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…
Andersonville
Event details
Saturday, May 2nd
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May2
Music & Comedy
Matteo Lane – We Gotta Catch Up! Tour
Matteo Lane is bringing his much‑anticipated “We Gotta Catch Up!” comedy tour to Chicago, performing at the historic The Chicago Theatre on May 2, 2026 at 7:00 PM. Hailing from the Chicago area,…
Loop
Event details
Saturday, May 2nd
7:00 p.m. – 9:00 p.m.
The Chicago Theatre
175 N. State
May2
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…
Old Town
Event details
Saturday, May 2nd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May2
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…
Old Town
Event details
Saturday, May 2nd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
May2
Music & Comedy
Katt Williams – Heaven On Earth Tour
On the heels of his explosive Netflix comedy special, WOKE FOKE, critically acclaimed comedian Katt Williams announces the HEAVEN ON EARTH TOUR. The upcoming tour…
West Loop
Event details
Saturday, May 2nd
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,
May2
Music & Comedy
Il Volo: North American 2026 Tour
Renowned Italian vocal trio IL Volo will perform live at Rosemont Theatre on May 2, 2026.
Event details
Saturday, May 2nd
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
May2
Music & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…
Event details
Saturday, May 2nd
8:00 p.m. – 11:00 p.m.
See all events in series
The Vic Theatre
3145 N. Sheffield
May2
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…
Lincoln Park
Event details
Saturday, May 2nd
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May2
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…
Lakeview
Event details
Saturday, May 2nd
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May 3, 2026: May3
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…
Event details
Sunday, May 3rd
6:00 p.m. – 7:30 p.m.
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The Lincoln Lodge
2040 North Milwaukee Avenue
May3
Music & Comedy
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders
The SatchVai Band, featuring iconic rock guitarists Joe Satriani and Steve Vai, is scheduled to perform in Chicago, IL, on Sunday, May 3, 2026, as…
Loop
Event details
Sunday, May 3rd
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
175 N. State
May3
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!)…
Old Town
Event details
Sunday, May 3rd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May3
Music & Comedy
Caifanes: 2026 Tour
Legendary Mexican rock band Caifanes is scheduled to perform in Chicago on Sunday, May 3, 2026.
Uptown
Event details
Sunday, May 3rd
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
May3
Music & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…
Event details
Sunday, May 3rd
8:00 p.m. – 11:00 p.m.
See all events in series
The Vic Theatre
3145 N. Sheffield
May 5, 2026: May5
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.…
Event details
Tuesday, May 5th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May5
Music & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
Pilsen
Event details
Tuesday, May 5th
8:00 p.m. – 11:00 p.m.
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Thalia Hall
1807 South Allport Street
May 6, 2026: May6
Music & Comedy
NewDad
Welcome to the iconic Metro Chicago, where on May 6, 2026, the indie-rock sensation NewDad will be taking the stage at 7:30 PM. Hailing from…
Event details
Wednesday, May 6th
7:30 p.m. – 9:30 p.m.
Metro Chicago
May6
Music & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
Pilsen
Event details
Wednesday, May 6th
8:00 p.m. – 11:00 p.m.
See all events in series
Thalia Hall
1807 South Allport Street