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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.…
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 DrMusic & Comedy
STAND-UP MOMEDY: Mother’s Day kickoff with Kristen Toomey
Moms. You know one. You have one. You may even BE one. They’re everywhere. And BOY, could they use a laugh. Luckily, we’ve got just what…
Friday, May 2nd
8:00 p.m. – 10:00 p.m.The Laughing Academy
3230 Glenview RoadMusic & 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 DrMusic & 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 StMusic & Comedy, Theatre & Performing Arts
Trapped in a Musical – an improvised musical
Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…
Friday, May 2nd
9:00 p.m. – 10:00 p.m.ComedySportz Chicago
929 W. Belmont Ave.Music & Comedy, Theatre & Performing Arts
Comedy Dance Chicago presents: 8-BITS
We’re back with all new bits! This joyful mixture of sketch comedy and dance is filled with a variety of characters that are sure to…
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,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.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 StreetFestivals, 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 StreetMusic & 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. RandolphMusic & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Saturday, May 3rd
6:00 p.m. – 7:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StFestivals, Fairs & Special Events, Music & Comedy
Glenn Raymond “Not A Safe Space” The Den Theatre
Presented by United By Comedy Join Stand up comedian Glenn Raymond as he brings his “Not A Safe Space Tour” to The Den Theatre. Be…
Saturday, May 3rd
5:00 p.m. – 7:00 p.m.The Den Theatre
1331 N Milwaukee AveMusic & 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.Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comedy in the Pocket
Get ready to laugh until your sides hurt at Comedy in the Pocket! Join us Saturday May 3rd at Surge Billiards for a lineup featuring…
Saturday, May 3rd
7:00 p.m. – 9:30 p.m.The Pocket at Surge Billiards Logan Square
3716 W. Fullerton Ave.Music & Comedy, Theatre & Performing Arts
RAD. a fun show.
May 3rd is Free Comic Book Day, and to celebrate, RAD is having a free special Saturday show. Same insanity but on the weekend! RAD. a fun…
Saturday, May 3rd
7:00 p.m. – 9:00 p.m.Graham Cracker Comics – Andersonville
5028 North Clark StreetMusic & 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 RoadFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts, Tours & Attractions
The Infinite Wrench is Off to the Races
Giddy on up and gallop on down to The Neo-Futurarium on Saturday, May 3rd at 3:00PM… because THE INFINITE WRENCH IS OFF TO THE RACES. In honor of the…
Saturday, May 3rd
3:00 p.m. – 4:30 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.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 AveMusic & 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. SheffieldMusic & 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. RandolphFestivals, 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 StMusic & Comedy, Theatre & Performing Arts
Hecklers’ Happy Hour
The only show in Chicago where you can tell the comedians what you really think! Audiences can unleash their inner “heckler” against some of Chicago’s…
Saturday, May 3rd
6:00 p.m. – 7:30 p.m.The Lincoln Lodge
2040 North Milwaukee Avenue
