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Teatro Zinzanni
May2
Music & 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 2, 2026
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May2
Music & 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 2, 2026
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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.
Baby Wants Candy! The Original Completely Improvised Musical
May2
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 May 2, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May2
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 May 2, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Improvised Shakespeare Company®
May2
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…

Saturday May 2, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Lincoln Lodge
May2
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…

Saturday May 2, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
May2
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 May 2, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Teatro Zinzanni
May3
Music & 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…

Sunday May 3, 2026
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
By A Thread: Nature’s Resilience
May3
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…

Sunday May 3, 2026
10:00 a.m.4:00 p.m.
By A Thread: Nature’s Resilience
May4
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…

Monday May 4, 2026
10:00 a.m.4:00 p.m.
By A Thread: Nature’s Resilience
May5
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…

Tuesday May 5, 2026
10:00 a.m.4:00 p.m.
Tuesday Good Show
May5
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 May 5, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
By A Thread: Nature’s Resilience
May6
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…

Wednesday May 6, 2026
10:00 a.m.4:00 p.m.
Tropical Wednesdays
May6
Tours & Attractions

Tropical Wednesdays

Immerge yourself in a cultural experience as Latin dances come alive on Taylor street – Salsa, Bachata, Cumbia, and Cha Cha Cha with margarita!

Wednesday May 6, 2026
6:00 p.m.8:00 p.m.
Vintage Bar Chicago
1449 W. Taylor St.
Hooch & Holler Comedy Show
May6
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday May 6, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
By A Thread: Nature’s Resilience
May7
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…

Thursday May 7, 2026
10:00 a.m.4:00 p.m.
Teatro Zinzanni
May7
Music & 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…

Thursday May 7, 2026
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Comedy Hour at Annoyance Theatre
May8
May9
Theatre & Performing Arts

Comedy Hour at Annoyance Theatre

Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…

Friday May 8, 2026
12:00 a.m.Saturday May 9, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
By A Thread: Nature’s Resilience
May8
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…

Friday May 8, 2026
10:00 a.m.4:00 p.m.
Teatro Zinzanni
May8
Music & 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…

Friday May 8, 2026
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May8
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 May 8, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
The Improvised Shakespeare Company®
May8
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 8, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
May8
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 8, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
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