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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 AveMusic & Comedy
Lavelle Dontae at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Please note: This is a special…
Friday, May 15th
9:00 p.m. – 10:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Friday Night in the SIDEBAR w/ The Meadowlark Lemons
Chicago blues/funk/soul band The Meadowlark Lemons released their debut, self-titled album on Friday, March 27. The band celebrated the release to a packed house at…
Friday, May 15th
9:00 p.m. – 11:00 p.m.Fitzgerald’s
6615 Roosevelt RoadMusic & 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
Laughter Hours: Late Night Jazzy-Themed Comedy Show
A late-night comedy showcase with a jazzy, lounge vibe featuring a live jazz musician and Chicago’s best comedians This is a showcase featuring some of…
Friday, May 15th
11:00 p.m. – 11:59 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & 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
Hecklers’ Happy Hour Comedy Show
Audiences can unleash their inner “heckler” against some of Chicago’s funniest comics in this chaotic standup showcase Hecklers’ Happy Hour aims to give audiences a…
Saturday, May 16th
6:00 p.m. – 7:15 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & 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
Jack Grady at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Jack Grady is a comedy magician…
Saturday, May 16th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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, Theatre & Performing Arts
Improvised Jane Austen
Improvised Jane Austen Improvised Jane Austen continues its entirely improvised tales of love and laughter. Audiences will enjoy an evening with wit and heart in…
Music & Comedy
“Ask a Comedian” Comedy Show w/ Kyrie Da Comic
“Connecting the Crowd to the Comics,” is the Motto! We’re bringing together top comedians and utilizing technology for an unforgettable show Join us for a…
Saturday, May 16th
7:30 p.m. – 9:00 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & 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
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
Chicago’s Best Comedy Show at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street,…
Saturday, May 16th
9:00 p.m. – 10:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611

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