Charlie Puth – Whatever’s Clever! World Tour 2026
May15
Music & Comedy

Charlie Puth – Whatever’s Clever! World Tour 2026

Grammy-nominated singer-songwriter Charlie Puth is scheduled to perform at Rosemont Theatre on Friday, May 15, 2026, as part of his global “Whatever’s Clever! World Tour”.

Friday, May 15th
7:30 p.m.11:30 p.m.
Rosemont Theatre
Devil’s Daughter
May15
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, May 15th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May15
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!

Friday, May 15th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
moonwatchers
May15
Jun1
Music & Comedy, Theatre & Performing Arts

moonwatchers

It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…

Friday, May 15th
8:00 p.m.Monday, June 1st
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Honk! A Short Form Improv Show
May15
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, May 15th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
420 Shakespeare
May15
Music & Comedy, Theatre & Performing Arts

420 Shakespeare

4 professional actors meet to perform a Shakespeare play… but only after one of them takes at least 20mg of you know what, leading to…

Friday, May 15th
9:00 p.m.10:30 p.m.
The De Matt Theater at The Second City
230 W North Ave
Voila: The Improvised Musical
May15
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, May 15th
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
May15
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, May 15th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
May16
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, May 16th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
Yellowcard – The Up Up Down Down 2026 Tour
May16
Music & Comedy

Yellowcard – The Up Up Down Down 2026 Tour

Alt-rock band Yellowcard will perform live at The Salt Shed Outdoors on May 16, 2026.

Saturday, May 16th
6:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Ava Logan — Jazz Zing!
May16
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Ava Logan — Jazz Zing!

Take a journey with me down a musical memory lane! The landscape is wide with music from Jazz to Latin to Blues and more, as…

Saturday, May 16th
7:00 p.m.
Haven Entertainment Center
932 East 43rd Street
The Infinite Wrench
May16
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, May 16th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Matt McCusker – Healing Frequency 2026 Tour
May16
Music & Comedy

Matt McCusker – Healing Frequency 2026 Tour

Comedian Matt McCusker is scheduled to perform in Chicago, IL, on Saturday, May 16, 2026, as part of his “The Healing Frequency Tour”

Saturday, May 16th
7:00 p.m.9:00 p.m.
The Riveria Theater
4746 N Racine Ave
Kid Rock – Freedom 250 Tour – The Road to Nashville
May16
Music & Comedy

Kid Rock – Freedom 250 Tour – The Road to Nashville

Kid Rock will bring his Freedom 250 Tour to the Chicago area on Saturday, May 16, 2026. This tour coincides with America’s 250th birthday and…

Saturday, May 16th
7:00 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
Baby Wants Candy! The Original Completely Improvised Musical
May16
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, May 16th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May16
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, May 16th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Bruno Mars – The Romantic Tour
May16
Music & Comedy

Bruno Mars – The Romantic Tour

16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.

Saturday, May 16th
7:30 p.m.11:30 p.m.
Soldier Field
1410 Special Olympics Drive
Ari Lennox – Vacancy Tour
May16
Music & Comedy

Ari Lennox – Vacancy Tour

Ari Lennox is bringing The Vacancy Tour to Chicago for a performance at The Chicago Theatre on Saturday, May 16, 2026.

Saturday, May 16th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
moonwatchers
May16
Jun2
Music & Comedy, Theatre & Performing Arts

moonwatchers

It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…

Saturday, May 16th
8:00 p.m.Tuesday, June 2nd
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Secret Sketch Show
May16
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, May 16th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
May16
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, May 16th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
I’m M$ B’Havin – Not Your Typical Mama … Memories of a Life Well Lived
May16
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

I’m M$ B’Havin – Not Your Typical Mama … Memories of a Life Well Lived

A mature Diva, I’m M$ B’Havin is built on a young woman’s frame; however, is not your typical Mama! She’ll give you the Blues, with…

Saturday, May 16th
9:30 p.m.11:00 p.m.
Stars & Garters
3914 N Clark St
Muse — Pure Magic
May17
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Muse — Pure Magic

Muse is a unique cabaret and burlesque experience with a focus on live music. The musings continue with 2026’s Chicago Cabaret Week! Join Boobs Radley,…

Sunday, May 17th
3:00 p.m.5:30 p.m.
Newport Theatre
956 W Newport Ave
Ruth Fuerst — Quirky (Quirky songs written by quirky songwriters sung by a quirky singer)
May17
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Ruth Fuerst — Quirky (Quirky songs written by quirky songwriters sung by a quirky singer)

Since when do irreverence and genuine warmth go together? Since “Quirky”! Come hear a mix of offbeat, funny, honest and uplifting songs about love, longing…

Sunday, May 17th
6:00 p.m.9:00 p.m.
Fulton Street Collective
1821 W Hubbard St UNIT 307