Dumb and Drummer
Feb19
Music & Comedy, Theatre & Performing Arts

Dumb and Drummer

Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…

Thursday February 19, 2026
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Improvsed DCOM
Feb19
Music & Comedy, Theatre & Performing Arts

Improvsed DCOM

Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…

Thursday February 19, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Roald Dahl’s The Enormous Crocodile: The Musical
Feb20
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…

Friday February 20, 2026
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
The Infinite Wrench
Feb20
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 February 20, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Feb20
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…

Friday February 20, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Feb20
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…

Friday February 20, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Teatro Zinzanni
Feb20
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…

Friday February 20, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Brandi Carlile Live at Allstate Arena – The Human 2026 Tour
Feb20
Music & Comedy

Brandi Carlile Live at Allstate Arena – The Human 2026 Tour

Acclaimed singer-songwriter Brandi Carlile brings The Human 2026 Tour to Allstate Arena in Rosemont on February 20, offering a night of emotionally charged performances and…

Friday February 20, 2026
7:00 p.m.10:00 p.m.
Allstate Arena
6920 Mannheim Road
Krampus: The Fright Before Christmas
Feb20
Festivals, Fairs & Special Events, Tours & Attractions

Krampus: The Fright Before Christmas

We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…

Friday February 20, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Devil’s Daughter
Feb20
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 February 20, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Feb20
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday February 20, 2026
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Trapped in a Musical – an improvised musical
Feb20
Music & 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 February 20, 2026
9:00 p.m.10:00 p.m.
Voila: The Improvised Musical
Feb20
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 February 20, 2026
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
Feb20
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 February 20, 2026
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
Feb21
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 February 21, 2026
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
Indoor Farmers Market
Feb21
Festivals, Fairs & Special Events

Indoor Farmers Market

As our outdoor season wraps up, we’re heading inside for the colder months. Come support local vendors and farmers, and stock up on your favorite…

Saturday February 21, 2026
10:00 a.m.2:00 p.m.
2800 N Milwaukee Ave
2800 N Milwaukee Ave
ComedySportz Chicago
Feb21
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 February 21, 2026
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
Feb21
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 February 21, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
Feb21
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 February 21, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
Feb21
Festivals, Fairs & Special Events, Tours & Attractions

Krampus: The Fright Before Christmas

We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…

Saturday February 21, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Baby Wants Candy! The Original Completely Improvised Musical
Feb21
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 February 21, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Feb21
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 February 21, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
ComedySportz Chicago
Feb21
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 February 21, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Best Of Annoyance Sketch
Feb21
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 February 21, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.