Bryan Torresdey at The Comedy Bar
Jan30
Music & Comedy

Bryan Torresdey at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Bryan Torresdey is a first-generation Mexican-American…

Friday, January 30th
9:00 p.m.11:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Stand-Up Showcase Showdown
Jan30
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Stand-Up Showcase Showdown

YOU MADE IT THROUGH JANUARY, NOW IT’S TIME TO REWARD YOURSELF WITH LAUGHS! The Stand-Up Showcase Showdown features some of Chicago’s best up-and-coming stand-up comedians…

Friday, January 30th
9:30 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
Jan30
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, January 30th
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
Jan30
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, January 30th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Roald Dahl’s The Enormous Crocodile: The Musical
Jan31
Music & Comedy, Theatre & Performing Arts

Roald Dahl’s The Enormous Crocodile: The Musical

The Enormous Crocodile musical brings Roald Dahl’s story to life with puppets, music, and laughs — a fun family show at Chicago’s Studebaker Theater. “For…

Saturday, January 31st
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
ComedySportz Chicago
Jan31
Music & 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, January 31st
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Hecklers Happy Hour
Jan31
Music & Comedy

Hecklers Happy Hour

Hecklers’ Happy Hour gives audiences a place to interact with comics, and comics a place to practice their crowd work—by targeting you! Chicago’s funniest comics…

Saturday, January 31st
6:00 p.m.7:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
The Infinite Wrench
Jan31
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, January 31st
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Kathleen Madigan – The Day Drinking 2025-26 Tour
Jan31
Music & Comedy

Kathleen Madigan – The Day Drinking 2025-26 Tour

Kathleen Madigan is scheduled to perform in Chicago on Saturday, January 31, 2026, at The Chicago Theatre. The show is part of her “The Day…

Saturday, January 31st
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Bryan Torresdey at The Comedy Bar
Jan31
Music & Comedy

Bryan Torresdey at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Bryan Torresdey is a first-generation Mexican-American…

Saturday, January 31st
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Teatro Zinzanni
Jan31
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Saturday, January 31st
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
Jan31
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, January 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Jan31
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, January 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Jane Austen
Jan31
Music & Comedy, Theatre & Performing Arts

Improvised Jane Austen

Celebrate Jane Austen’s birthday all winter long with Improvised Jane Austen! Just one day cannot encapsulate a proper observation of Jane Austen’s life and work.…

Saturday, January 31st
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
Evan Plus One: Party Animals
Jan31
Music & Comedy

Evan Plus One: Party Animals

Evan Plus One: Party AnimalsWinners of Season 38 of The Original Improv Gladiators Get ready for a night of improv worthy of a celebration! Evan…

Saturday, January 31st
7:30 p.m.8:30 p.m.
Cornservatory
4210 N Lincoln Ave
New Year New Show
Jan31
Music & Comedy, Theatre & Performing Arts

New Year New Show

New Year! New Show! Welcome to 2026 where the laughter runs hot and the jokes run cheap. Every week is a brand new sketch show,…

Saturday, January 31st
8:00 p.m.9:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
ComedySportz Chicago
Jan31
Music & 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, January 31st
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Jan31
Music & Comedy, Theatre & Performing Arts

The Cosmic Underground Show

The Cosmic Underground Show blasts off for a 90-minute immersive comedy, magic, and mind-reading show. Cosmic founders Harrison Lampert (a quirky sleight-of-hand expert) and Kayla…

Saturday, January 31st
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Secret Sketch Show
Jan31
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, January 31st
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Bryan Torresdey at The Comedy Bar
Jan31
Music & Comedy

Bryan Torresdey at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Bryan Torresdey is a first-generation Mexican-American…

Saturday, January 31st
9:00 p.m.11:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Best Of Annoyance Sketch
Jan31
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, January 31st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Così fan tutte
Feb1
Music & Comedy, Theatre & Performing Arts

Così fan tutte

Two officers, convinced all women are fickle in love, hatch a plan to switch places and woo each other’s fiancées in disguise — but the…

Sunday, February 1st
2:00 p.m.5:30 p.m.
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Teatro Zinzanni
Feb1
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Sunday, February 1st
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
A musical tribute to “Paris in Black”
Feb1
Music & Comedy

A musical tribute to “Paris in Black”

We are celebrating the awe-inspiring exhibit of Paris in Black. Join Black Voices in Cabaret and fellow performers returning from the Chicago Paris Cabaret Connexion in France as we…

Sunday, February 1st
4:30 p.m.8:00 p.m.
DuSable Black History Museum and Education Center
740 E 56th Place