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Upcoming Chicago Events

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ComedySportz Chicago
Jun14
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, June 14th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ricky Sim: Coming Out To Dead People
Jun14
Music & Comedy, Theatre & Performing Arts

Ricky Sim: Coming Out To Dead People

Following sold-out shows and multiple rave reviews at the Edinburgh Fringe Festival, London’s Soho Theatre, and Off-Broadway at Soho Playhouse, comedian and storyteller Ricky Sim…

Saturday, June 14th
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Natalia Lafourcade – Cancionera Tour
Jun14
Music & Comedy

Natalia Lafourcade – Cancionera Tour

Natalia Lafourcade brings the Cancionera Tour to The Chicago Theatre on Saturday, June 14.

Saturday, June 14th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
Jun14
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, June 14th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Jun14
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, June 14th
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
Jun14
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, June 14th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Kieron Harrell & Friends
Jun14
Music & Comedy

Kieron Harrell & Friends

Kieron Harrell is a Chicago comedian who was born and raised in Ohio, but like anyone trying to succeed in life, he first had to leave…

Saturday, June 14th
10:00 p.m.11:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Jun15
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 15th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
Jun15
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 15th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Jun15
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 15th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Glenwood Sunday Market in Rogers Park
Jun15
Festivals, Fairs & Special Events

Glenwood Sunday Market in Rogers Park

The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…

Sunday, June 15th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Andersonville Midsommarfest
Jun15
Festivals, Fairs & Special Events

Andersonville Midsommarfest

Summer. Starts. HERE. Midsommarfest returns to Andersonville for its 59th year—and it’s your official invitation to celebrate in the streets and kick off Pride season…

Sunday, June 15th
12:00 p.m.9:00 p.m.
Clark Street from Foster to Gregory
Rush Hour Concerts | | Merida Trio
Jun15
Music & Comedy

Rush Hour Concerts | | Merida Trio

RUSH HOUR CONCERTS | | MERIDA TRIO Charlene Kluegel, violin Jean Hatmaker, cello Katherine Petersen, piano Program  Franz Schubert – Piano Trio in B-flat major,…

Sunday, June 15th
5:45 p.m.6:30 p.m.
Don’t Call Me White Girl
Jun15
Music & Comedy

Don’t Call Me White Girl

Mona Love is a comedian and podcast host of the ‘Don’t Call Me White Girl’ show. She is known for giving advice and her commentary…

Sunday, June 15th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Father’s Day Comedy Show: Doing Our Moms – OOPS, All Dads!
Jun15
Music & Comedy, Theatre & Performing Arts

Father’s Day Comedy Show: Doing Our Moms – OOPS, All Dads!

It’s time for the second annual Father’s Day edition of Doing Our Moms: Oops, All Dads! In a usual Doing Our Moms show, host Judy Anderson [her daughter, Chicago comic…

Sunday, June 15th
7:30 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Natalia Lafourcade – Cancionera Tour
Jun15
Music & Comedy

Natalia Lafourcade – Cancionera Tour

Natalia Lafourcade brings the Cancionera Tour to The Chicago Theatre on June 15, 2025.

Sunday, June 15th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Division Street Farmers Market
Jun16
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 16th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Rush Hour Concerts | | Merida Trio
Jun16
Music & Comedy

Rush Hour Concerts | | Merida Trio

RUSH HOUR CONCERTS | | MERIDA TRIO Charlene Kluegel, violin Jean Hatmaker, cello Katherine Petersen, piano Program  Franz Schubert – Piano Trio in B-flat major,…

Monday, June 16th
5:45 p.m.6:30 p.m.
Summer Screenings: Free Films All Summer Long
Jun16
Sep3
Festivals, Fairs & Special Events

Summer Screenings: Free Films All Summer Long

🍿 The Summer Screenings program is back with free screenings of 21 films from 21 countries! This year’s theme is Summer of Love! Love has…

Monday, June 16th
6:30 p.m.Wednesday, September 3rd
9:00 p.m.
Chicago Cultural Center and Chicago History Museum
Magic Mondays
Jun16
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, June 16th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Set Sail with Blues Hall of Famer Michael Charles and His Band
Jun16
Music & Comedy, Sports & Recreation, Tours & Attractions

Set Sail with Blues Hall of Famer Michael Charles and His Band

“Join the power trio of Australian born, Chicago Blues Hall of Famer Michael Charles as he embarks on the Tall Ship Windy for the Monday…

Monday, June 16th
7:00 p.m.9:00 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Monday Night Concert Series
Jun16
Music & Comedy, Tours & Attractions

Monday Night Concert Series

Chase Away your Monday Blues with a Symphony of Soul! We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you…

Monday, June 16th
7:00 p.m.9:00 p.m.
Navy Pier 600 East Grand Avenue Chicago, IL
600 East Grand Avenue
Late Nite Mic with Vik Pandya at The Comedy Bar
Jun16
Music & Comedy

Late Nite Mic with Vik Pandya at The Comedy Bar

IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…

Monday, June 16th
7:30 p.m.9:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Ben Folds & Chicago Symphony Orchestra
Jun16
Music & Comedy

Ben Folds & Chicago Symphony Orchestra

Emmy-award nominated composer, singer-songwriter, and pianist Ben Folds joins the Chicago Symphony Orchestra for a night of exceptional performances. Widely regarded as one of the…

Monday, June 16th
7:30 p.m.10:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
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