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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 TheatreMusic & 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.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.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 AvenueMusic & 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 StMusic & 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 AveMusic & 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,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.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.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, ILFestivals, 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 StreetMusic & 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.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 AveMusic & 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 AveMusic & 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…
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 FloorMusic & 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 DriveMusic & 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. StateMusic & 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 AvenueMusic & 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…
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.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 StFestivals, 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 AveFestivals, 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

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