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Upcoming Chicago Events

Check out what's happening all around Chicago.

Division Street Farmers Market
May19
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, May 19th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Magic Mondays
May19
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, May 19th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Division Street Farmers Market
May20
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, May 20th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Tuesday Good Show
May20
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 20th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Billy Idol & Joan Jett and The Blackhearts – It’s A Nice Day To…Tour Again!
May20
Music & Comedy

Billy Idol & Joan Jett and The Blackhearts – It’s A Nice Day To…Tour Again!

Billy Idol & Joan Jett and The Blackhearts will perform live at Credit Union 1 Amphitheatre on May 20, 2025.

Tuesday, May 20th
7:30 p.m.10:30 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
Division Street Farmers Market
May21
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.

Wednesday, May 21st
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Peter Pan at Chicago Kids Company
May21
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Wednesday, May 21st
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
Fleurs de Villes Downton Abbey
May21
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Fleurs de Villes Downton Abbey

Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…

Wednesday, May 21st
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Hooch & Holler Comedy Show
May21
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 21st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Division Street Farmers Market
May22
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.

Thursday, May 22nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Peter Pan at Chicago Kids Company
May22
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Thursday, May 22nd
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
Fleurs de Villes Downton Abbey
May22
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Fleurs de Villes Downton Abbey

Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…

Thursday, May 22nd
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Teatro Zinzanni
May22
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 22nd
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Nikki Glaser: Alive And Unwell Tour
May22
Music & Comedy

Nikki Glaser: Alive And Unwell Tour

Nikki Glaser will bring the ALIVE AND UNWELL TOUR to The Chicago Theatre on May 22, May 31 and June 1.

Thursday, May 22nd
7:00 p.m.9:00 p.m.
Chicago Theatre
Sydney Castillo at The Comedy Bar
May22
Music & Comedy

Sydney Castillo at The Comedy Bar

Sydney Castillo is a stand-up comedian, actor, producer, and writer. He most recently wrote on HBO’s GAME THEORY and VH1’s CELEBRITY SQUARES. He was part of…

Thursday, May 22nd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Post Malone: The BIG ASS Stadium Tour
May22
Music & Comedy

Post Malone: The BIG ASS Stadium Tour

Post Malone announced his upcoming tour includes a show at Wrigley Field in 2025! His debut performance at the Friendly Confines is scheduled for Thursday,…

Thursday, May 22nd
7:30 p.m.10:30 p.m.
Wrigley Field
1060 West Addison Street
Secret Family
May22
Music & Comedy

Secret Family

Secret Family is a sketch comedy group that’s exactly like a real family, only our drama and infighting is mostly pretend, and our love for…

Thursday, May 22nd
8:00 p.m.9:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Division Street Farmers Market
May23
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.

Friday, May 23rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Fleurs de Villes Downton Abbey
May23
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Fleurs de Villes Downton Abbey

Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…

Friday, May 23rd
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Wicker Park Bucktown’s “First Fridays” Art Walk
May23
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, May 23rd
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Teatro Zinzanni
May23
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 23rd
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May23
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 23rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Grossman Ensemble – World Premieres III
May23
Music & Comedy, Theatre & Performing Arts

Grossman Ensemble – World Premieres III

Esteemed conductor Tim Weiss returns to lead the Grossman Ensemble for an eagerly anticipated third collaboration. Composers Christopher Stark, whose music The New York Times has called, “fetching…

Friday, May 23rd
7:30 p.m.9:00 p.m.
Logan Center for the Arts – Performance Hall
915 E. 60th St.
An Evening with Vince Gill
May23
Music & Comedy

An Evening with Vince Gill

Vince Gill will perform at The Chicago Theatre on Friday, May 23.

Friday, May 23rd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
bean-night

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