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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 8th
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 8th
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 9th
10:00 a.m. – 11:30 a.m.Stars & Garters Theater
3914 N. Clark St.Music & Comedy, Theatre & Performing Arts
Dinner Detective Murder Mystery Show
The Dinner Detective is an interactive true crime murder mystery show set in the present day and based on real cold cases. Feast on a…
Saturday, May 9th
6:00 p.m. – 9:00 p.m.Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario StMusic & Comedy
Disclosure: Spring 2026 North America Tour
Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.
Saturday, May 9th
6:30 p.m. – 9:30 p.m.The Salt Shed
1357 N Elston Ave, Chicago, ILMusic & 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 9th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy
Gus Constantellis at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…
Saturday, May 9th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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 9th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy
Saturday Night’s Alright For Improv
Saturday Night’s Alright for Improv and Corn Productions is the best place to see it! Two Saturdays, two amazing line-ups, one great host. Hosted by…
Music & Comedy, Theatre & Performing Arts
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
Music & Comedy
DiDonato Performs Neruda Songs
In her final program as 2025/26 CSO Artist-in-Residence, Joyce DiDonato — one of today’s most compelling operatic storytellers — brings extraordinary emotional depth to Neruda Songs,…
Saturday, May 9th
7:30 p.m. – 9:30 p.m.Chicago Symphony Center
220 S Michigan AveMusic & Comedy
Peso Pluma – Dinastia Tour 2026
Mexican music star Peso Pluma is scheduled to perform in Chicago on May 8-9, 2026, as the grand finale of his North American “DINASTÍA by…
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 9th
8:00 p.m. – Tuesday, May 26th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy
Alejandro Fernandez – de Rey a Rey Tour
Alejandro Fernández is bringing his de Rey a Rey tour, a tribute to the music of his late father, the legendary Vicente Fernández, to Allstate…
Saturday, May 9th
8:30 p.m. – 11:30 p.m.Allstate Arena
6920 Mannheim RoadMusic & Comedy
Gus Constantellis at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…
Saturday, May 9th
9:00 p.m. – 10:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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 9th
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.Music & Comedy
Chicago Comedy Hour
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
Saturday, May 9th
9:30 p.m. – 10:30 p.m.The De Matt Theater at The Second City
230 W North AveFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Sonia Oyola & Bob Solone – Love Songs for You
Sonia Oyola and Bob Solone are excited to share more of their favorite love songs and duets in English/Spanish. Their shows always feature an eclectic,…
Sunday, May 10th
4:00 p.m. – 6:00 p.m.Le Piano
6970 N. Glenwood Ave.Music & Comedy
Mother’s Day Celebration with Tamela Mann
COME CELEBRATE MOTHERS DAY AT THE HOUSE OF HOPE. Come to The Mothers Day Celebration at The House Of Hope. Treat the Mother In Your…
Sunday, May 10th
6:00 p.m. – 11:00 p.m.House Of Hope
752 E 114th StMusic & Comedy
Disclosure: Spring 2026 North America Tour
Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.
Sunday, May 10th
6:30 p.m. – 9:30 p.m.The Salt Shed
1357 N Elston Ave, Chicago, ILMusic & Comedy, Theatre & Performing Arts
GossNight Chicago
Think Deep, Laugh Hard and Go Home Happy It’s just a big game of telephone! And… GossNight brings people together through laughter and shared curiosity…
Sunday, May 10th
7:00 p.m. – 8:30 p.m.Bramble Arts LoftMusic & Comedy
Phylicia Dshea at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Phylicia Dshea has gained popularity on…
Sunday, May 10th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611

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