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
Lavelle Dontae at The Comedy Bar
May15
Music & 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 60611
Friday Night in the SIDEBAR w/ The Meadowlark Lemons
May15
Music & 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 Road
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.
Laughter Hours: Late Night Jazzy-Themed Comedy Show
May15
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 States
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.
Hecklers’ Happy Hour Comedy Show
May16
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 States
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.
Jack Grady at The Comedy Bar
May16
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 60611
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
Improvised Jane Austen
May16
Music & 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…

Saturday, May 16th
7:30 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
“Ask a Comedian” Comedy Show w/ Kyrie Da Comic
May16
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 States
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
May16
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…

Saturday, May 16th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
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.
Chicago’s Best Comedy Show at The Comedy Bar
May16
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