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The Infinite Wrench
May2
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…

Friday, May 2nd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Barry Brewer Jr at The Comedy Bar
May2
Music & Comedy

Barry Brewer Jr at The Comedy Bar

Barry Brewer hails as one of Hollywood’s most talented, up and coming stars. Best known for his breakout television role as the lead in Tyler…

Friday, May 2nd
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Jahari Stampley Trio
May2
Music & Comedy

Jahari Stampley Trio

About the Performance While people Jahari Stampley’s age may be quipping about staving off quarter-life crises, the 25-year-old Chicago-native pianist is understandably more focused on…

Friday, May 2nd
7:30 p.m.9:00 p.m.
Ravinia Festival
418 Sheridan Road
Lucy Dacus – Forever Is A Feeling Tour
May2
Music & Comedy

Lucy Dacus – Forever Is A Feeling Tour

Indie singer-songwriter Lucy Dacus brings the Forever is a Feeling Tour to The Chicago Theatre on May 2.

Friday, May 2nd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Devil’s Daughter
May2
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 2nd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
R&B Invitation Tour
May2
Music & Comedy

R&B Invitation Tour

The R&B Invitation Tour, featuring R&B legends Joe, Musiq Soulchild and Eric Benét, will take over the Arie Crown Theater in Chicago on May 2, 2025, for an evening of smooth vocals and timeless…

Friday, May 2nd
8:00 p.m.10:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
R&B Invitation Tour: Joe, Musiq Soulchild & Eric Benet
May2
Music & Comedy

R&B Invitation Tour: Joe, Musiq Soulchild & Eric Benet

The R&B Invitation Tour, featuring R&B legends Joe, Musiq Soulchild and Eric Benét, will take over the Arie Crown Theater in Chicago on May 2,…

Friday, May 2nd
8:00 p.m.11:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
Lowkey Funny Comedy Show
May2
Music & Comedy, Theatre & Performing Arts

Lowkey Funny Comedy Show

This monthly show will shine light on some of Chicago’s emerging talent in stand-up, improv/ sketch comedy, and up and coming music artists. Break away…

Friday, May 2nd
8:30 p.m.11:00 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Voila: The Improvised Musical
May2
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 2nd
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
May2
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 2nd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
May3
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday, May 3rd
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
WindSync
May3
Music & Comedy

WindSync

About the Performance WindSync embraces classics from across centuries of music writing, using their vibrant “fourth wall”-breaking approach to performance to make standard repertoire a…

Saturday, May 3rd
3:00 p.m.5:00 p.m.
Ravinia Festival
418 Sheridan Road
Down & Derby at Utopian Tailgate
May3
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

Down & Derby at Utopian Tailgate

Enjoy a lively Kentucky Derby watch party in perfect form at Utopian Tailgate; Old Town’s premier rooftop and high-energy party landscape. Saturday, May 3rd  * …

Saturday, May 3rd
3:00 p.m.6:00 p.m.
Utopian Tailgate
1608 North Wells Street
Kentucky Derby Watch Party at Joy District Rooftop
May3
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation, Tours & Attractions

Kentucky Derby Watch Party at Joy District Rooftop

Enjoy the Kentucky Derby with a “Grand Stand” experience at the Rooftop of JOY District.  This picture-perfect setting is sure to deliver a high-roller’s party scene like no other.…

Saturday, May 3rd
3:00 p.m.6:00 p.m.
Joy District
112 W Hubbard St
Kentucky Derby Watch Party at J. Parker
May3
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation, Tours & Attractions

Kentucky Derby Watch Party at J. Parker

Enjoy the Kentucky Derby with no stakes and high limits at The J. Parker Rooftop.  This Lincoln park attraction is sure to impress with its indoor/outdoor viewing…

Saturday, May 3rd
3:00 p.m.6:00 p.m.
The J. Parker
1816 North Clark Street
Teatro Zinzanni
May3
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday, May 3rd
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May3
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 3rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Glenn Raymond “Not Safe Space”
May3
Music & Comedy

Glenn Raymond “Not Safe Space”

GLENN RAYMOND “NOT A SAFE SPACE” Presented by  United By Comedy Join us for a night of comedy with stand-up comedian Glenn Raymond, who is…

Saturday, May 3rd
7:00 p.m.8:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
Bruce Bruce – Stay In Your Lane *Comedy Special Taping*
May3
Music & Comedy, Theatre & Performing Arts

Bruce Bruce – Stay In Your Lane *Comedy Special Taping*

With his place cemented as one of the true legends of comedy, comedian Bruce Bruce continues his career as one of the best in his…

Saturday, May 3rd
7:00 p.m.11:30 p.m.
The Vic Theatre
3145 N. Sheffield
Baby Wants Candy! The Original Completely Improvised Musical
May3
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 3rd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May3
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 3rd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
South Chicago Dance Theatre
May3
Music & Comedy

South Chicago Dance Theatre

Experience “note by note precision” (Dance Magazine) with South Chicago Dance Theatre in their return to The Auditorium stage. Be moved by an electric fusion of classical and…

Saturday, May 3rd
7:30 p.m.9:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Heather McMahan – Bamboozled Tour
May3
Music & Comedy

Heather McMahan – Bamboozled Tour

Heather McMahan will bring The Bamboozled Tour to The Chicago Theatre on Saturday, May 3.

Saturday, May 3rd
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
May3
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 3rd
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
bean-night

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