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Upcoming Chicago Events

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Teatro Zinzanni
May31
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 31st
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May31
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 31st
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May31
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 31st
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Miss Renee Live One Night Only
May31
Music & Comedy

Miss Renee Live One Night Only

HollywoodGenGen, widely recognized as “Miss Renee”, is an acclaimed actor, comedian, and social media influencer celebrated for their ability to connect with audiences through humor and…

Saturday, May 31st
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Nikki Glaser: Alive And Unwell Tour
May31
Music & Comedy

Nikki Glaser: Alive And Unwell Tour

Nikki Glaser will bring the ALIVE AND UNWELL TOUR to The Chicago Theatre on May 31 and June 1.

Saturday, May 31st
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
The Weeknd: After Hours Til Dawn Tour With Playboi Carti And Mike Dean
May31
Music & Comedy

The Weeknd: After Hours Til Dawn Tour With Playboi Carti And Mike Dean

Global superstar The Weeknd will embark on a brand-new stadium tour across North America this year featuring chart-topping, multi-platinum and genre-defying Atlanta rapper Playboi Carti…

Saturday, May 31st
7:00 p.m.10:00 p.m.
Soldier Field
1410 Special Olympics Dr, Chicago, IL 60605
Baby Wants Candy! The Original Completely Improvised Musical
May31
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 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May31
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 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Here 4 A Bit *Naughty Improv
May31
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 31st
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
May31
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 31st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May31
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, May 31st
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Orbit
May31
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Saturday, May 31st
11:00 p.m.11:30 p.m.
iO Theater
1501 N. Kingsbury St.
Teatro Zinzanni
Jun1
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, June 1st
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
Jun1
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, June 1st
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Jun1
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Sunday, June 1st
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Chicago ScavHunt 2025: Flavors of the City
Jun1
Festivals, Fairs & Special Events

Chicago ScavHunt 2025: Flavors of the City

From May 30th – June 1st, downtown Chicago streets will be occupied by explorers and scavenger hunters competing in the 4th Annual eATLAS Adventures to…

Sunday, June 1st
10:00 a.m.9:00 p.m.
Downtown Chicago
Porchfest Lakeview
Jun1
Festivals, Fairs & Special Events, Theatre & Performing Arts

Porchfest Lakeview

Porhcfest is a music festival that takes place on front porches. With neighbors hosting the concerts and local musicians performing, it captures the essence of…

Sunday, June 1st
1:00 p.m.5:00 p.m.
West Lakeview
Corner of Lincoln & Marshfield
Blackswan Fan Tour Concert
Jun1
Music & Comedy

Blackswan Fan Tour Concert

BLACKSWAN US FAN CONCERT 2025 TOUR – Lumina’s Light! 🦢 Blackswan is a South Korean multinational girl group. This four-member girl group is the world’s…

Sunday, June 1st
6:30 p.m.9:00 p.m.
Harold Washington Cultural Center
4701 S. King Drive
Nikki Glaser: Alive And Unwell Tour
Jun1
Music & Comedy

Nikki Glaser: Alive And Unwell Tour

Nikki Glaser will bring the ALIVE AND UNWELL TOUR to The Chicago Theatre on May 31 and June 1.

Sunday, June 1st
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Division Street Farmers Market
Jun2
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Monday, June 2nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Division Street Farmers Market
Jun3
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Tuesday, June 3rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Celebrating Jacques Pépin’s 90th Birthday at Asador Bastian
Jun3
Festivals, Fairs & Special Events

Celebrating Jacques Pépin’s 90th Birthday at Asador Bastian

This celebration is part of a nationwide series of 90 dinners leading up to Jacques Pépin’s 90th birthday in December 2025. The campaign, which preserves,…

Tuesday, June 3rd
6:00 p.m.10:00 p.m.
Asador Bastian
214 West Erie St
Tuesday Good Show
Jun3
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, June 3rd
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Ron Chernow on Mark Twain
Jun3
Festivals, Fairs & Special Events

Ron Chernow on Mark Twain

Acclaimed author Ron Chernow, of Hamilton fame, is one of the most renowned voices in history and politics. Recipient of the 2015 National Humanities Medal,…

Tuesday, June 3rd
7:00 p.m.8:30 p.m.
First United Methodist Church at the Chicago Temple
77 W Washington St
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