Voila: The Improvised Musical
Feb27
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 27, 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
Feb27
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 27, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Indoor Farmers Market
Feb28
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 28, 2026
10:00 a.m.2:00 p.m.
2800 N Milwaukee Ave
2800 N Milwaukee Ave
ComedySportz Chicago
Feb28
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 28, 2026
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Nothing More – Carnal Nature 2026 World Tour
Feb28
Music & Comedy

Nothing More – Carnal Nature 2026 World Tour

Triple-Grammy-nominated outfit Nothing More/w special guests Catch Your Breath, Archers & Doobie will perform live at Riviera Theatre on Feb. 28, 2026.

Saturday February 28, 2026
6:30 p.m.10:00 p.m.
The Riveria Theater
4746 N Racine Ave
The Infinite Wrench
Feb28
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 28, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sherri Shepherd
Feb28
Music & Comedy

Sherri Shepherd

Welcome to the Vic Theatre in Chicago, Illinois, where the talented Sherri Shepherd will be gracing the stage on February 28, 2026, at 7:00 PM.…

Saturday February 28, 2026
7:00 p.m.9:00 p.m.
The Vic Theatre
3145 N. Sheffield
Teatro Zinzanni
Feb28
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 28, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
Feb28
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 28, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Baby Wants Candy! The Original Completely Improvised Musical
Feb28
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 28, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Feb28
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 28, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Margo Price
Feb28
Music & Comedy

Margo Price

Welcome to Metro Chicago, where the vibrant music scene and top-notch entertainment collide! Join us on February 28, 2026, at 7:30 PM for an unforgettable…

Saturday February 28, 2026
7:30 p.m.9:30 p.m.
Metro Chicago
ComedySportz Chicago
Feb28
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 28, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Miguel Live In Chicago – Caos Tour 2026
Feb28
Music & Comedy

Miguel Live In Chicago – Caos Tour 2026

Chart-topping artist Miguel is bringing his signature blend of soul, funk, and rock to Chicago on February 28, 2026, with a headline show at Byline…

Saturday February 28, 2026
8:00 p.m.11:00 p.m.
Best Of Annoyance Sketch
Feb28
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 28, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Indoor Farmers Market at Water Tower Place
Mar1
Festivals, Fairs & Special Events

The Indoor Farmers Market at Water Tower Place

For the second year in a row, Chicago’s Water Tower Place is teaming up with the South Loop Farmers Market to bring its popular indoor…

Sunday March 1, 2026
12:00 p.m.4:00 p.m.
Water Tower Place
835 N Michigan Ave
Teatro Zinzanni
Mar1
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 March 1, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
Mar1
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 March 1, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
Mar1
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…

Sunday March 1, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Wheel of Improv
Mar1
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday March 1, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Krampus: The Fright Before Christmas
Mar2
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…

Monday March 2, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Tuesday Good Show
Mar3
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday March 3, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Krampus: The Fright Before Christmas
Mar3
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…

Tuesday March 3, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Lauren Spencer Smith at Byline Bank Aragon Ballroom
Mar3
Music & Comedy

Lauren Spencer Smith at Byline Bank Aragon Ballroom

Lauren Spencer Smith is set to light up the Byline Bank Aragon Ballroom in Chicago, Illinois, on Tuesday, March 3rd, 2026. Feel all the emotion…

Tuesday March 3, 2026
8:00 p.m.10:00 p.m.