Teatro Zinzanni
May1
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 May 1, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
May1
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 May 1, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
The Improvised Shakespeare Company®
May1
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Friday May 1, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Isaiah Collier: In Tribute to the Classics of John Coltrane
May1
Music & Comedy

Isaiah Collier: In Tribute to the Classics of John Coltrane

Isaiah Collier’s saxophone sound is both fierce and deeply reflective—rooted in tradition yet stretching toward the future. Named Chicago Tribune’s Jazz Artist of the Year and…

Friday May 1, 2026
7:30 p.m.9:00 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Out Here
May1
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Friday May 1, 2026
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May1
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Friday May 1, 2026
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Devil’s Daughter
May1
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 1, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May1
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 May 1, 2026
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Lincoln Lodge
May1
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Friday May 1, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Demi Lovato Live at United Center – It’s Not That Deep Tour 2026
May1
Music & Comedy

Demi Lovato Live at United Center – It’s Not That Deep Tour 2026

Award-winning diva Demi Lovato brings her powerhouse voice and fearless stage presence to Chicago on May 1, 2026, for a one-night-only performance at the United…

Friday May 1, 2026
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Voila: The Improvised Musical
May1
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 1, 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
May1
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 1, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Play For All at Chicago Children’s Museum
May2
Museums, Galleries & Exhibitions

Play For All at Chicago Children’s Museum

Play For All Saturday, April 5 at 10 am First Saturday of Every Month (through June 2026)   Chicago Children’s Museum’s Play For All initiative…

Saturday May 2, 2026
10:00 a.m.12:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
Indoor Farmers Market
May2
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 May 2, 2026
10:00 a.m.2:00 p.m.
2800 N Milwaukee Ave
2800 N Milwaukee Ave
By A Thread: Nature’s Resilience
May2
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Saturday May 2, 2026
10:00 a.m.4:00 p.m.
Illinois Holocaust Museum presents Experience360
May2
Museums, Galleries & Exhibitions

Illinois Holocaust Museum presents Experience360

Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…

Saturday May 2, 2026
10:00 a.m.5:00 p.m.
Illinois Holocaust Museum presents Experience360
360 N State St
American Prophets: Writers, Religion, and Culture
May2
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Saturday May 2, 2026
10:00 a.m.5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Seadog Architecture Tour on the Chicago River
May2
Tours & Attractions

Seadog Architecture Tour on the Chicago River

Soak in unobstructed views of Chicago’s world-famous architecture with an exciting 45-minute ride on our Seadog Chicago River Architecture Tour! Starting right on the Chicago…

Saturday May 2, 2026
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
Out Here
May2
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Saturday May 2, 2026
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May2
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Saturday May 2, 2026
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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…

Saturday May 2, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Matteo Lane – We Gotta Catch Up! Tour
May2
Music & Comedy

Matteo Lane – We Gotta Catch Up! Tour

Matteo Lane is bringing his much‑anticipated “We Gotta Catch Up!” comedy tour to Chicago, performing at the historic The Chicago Theatre on May 2, 2026 at 7:00 PM. Hailing from the Chicago area,…

Saturday May 2, 2026
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
The Great Gatsby
May2
Theatre & Performing Arts

The Great Gatsby

THE PARTY’S ROARING IN CHICAGO! THE GREAT GATSBY is a “Broadway extravaganza that explodes with life and energy” (Entertainment Weekly). Based on the classic American novel…

Saturday May 2, 2026
7:00 p.m.9:30 p.m.
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Teatro Zinzanni
May2
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 May 2, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St