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Upcoming Chicago Events

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A Gallery of Dances
Jun21
Theatre & Performing Arts

A Gallery of Dances

A gallery is not just a place where art lives, it is a place where stories are brought to life through paint strokes, photos, and…

Saturday, June 21st
8:00 p.m.9:30 p.m.
Chicago Danztheatre Ensemble
1650 W Foster Ave
ComedySportz Chicago
Jun21
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 21st
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ryan Adams: Heartbreaker ’25 World Tour
Jun21
Music & Comedy

Ryan Adams: Heartbreaker ’25 World Tour

Singer-songwriter Ryan Adams will perform live at The Chicago Theatre on June 21, 2025.

Saturday, June 21st
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
Jun21
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 21st
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky
Jun21
Tours & Attractions

Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in…

Saturday, June 21st
9:00 p.m.10:30 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Best Of Annoyance Sketch
Jun21
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 21st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Al Jackson at The Comedy Bar
Jun21
Music & Comedy

Al Jackson at The Comedy Bar

Al Jackson is a Los Angeles-based stand-up comedian, writer, and TV/radio personality best known for his special “Comedy Central Presents: Al Jackson” and for his role…

Saturday, June 21st
9:30 p.m.11:00 p.m.
The Comedy Bar
500 N. LaSalle St.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Jun21
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 21st
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Franz West: Millennium Park
Jun22
Museums, Galleries & Exhibitions, Tours & Attractions

Franz West: Millennium Park

Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…

Sunday, June 22nd
Millennium Park
201 E Randolph St
See Chicago Dance’s Chicago Dance Month Returns This June
Jun22
Theatre & Performing Arts

See Chicago Dance’s Chicago Dance Month Returns This June

See Chicago Dance, the dance industry’s nonprofit service organization celebrating its 20th anniversary in 2025, is proud to announce that its popular annual offering, Chicago…

Sunday, June 22nd
Various locations
Teatro Zinzanni
Jun22
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 22nd
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
Jun22
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 22nd
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Jun22
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 22nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Seeing Connections: The Art of Richard Penn
Jun22
Museums, Galleries & Exhibitions

Seeing Connections: The Art of Richard Penn

Inspiration for art can come from many sources. Retired University of Chicago Medicine neurosurgeon and artist Richard Penn finds inspiration in nature, philosophy, science, and…

Sunday, June 22nd
9:00 a.m.4:45 p.m.
Special Collections Research Center Exhibition Gallery
1100 East 57th Street
Dressed in History: A Costume Collection Retrospective
Jun22
Museums, Galleries & Exhibitions, Tours & Attractions

Dressed in History: A Costume Collection Retrospective

What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…

Sunday, June 22nd
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
Flight of Butterflies
Jun22
Museums, Galleries & Exhibitions

Flight of Butterflies

ntroducing the Flight of Butterflies! This city-wide exhibit merges nature, art, and story telling, creating a memorable experience for all in Chicago. Local artists adorn…

Sunday, June 22nd
10:00 a.m.4:00 p.m.
Tom Torluemke: LIVE! ON PAPER, 1987 – 2024
Jun22
Museums, Galleries & Exhibitions

Tom Torluemke: LIVE! ON PAPER, 1987 – 2024

Tom Torluemke is a contemporary artist whose practice spans 40+ years and includes works in painting, drawing, sculpture, performance, and various mediums. Tom is known…

Sunday, June 22nd
10:00 a.m.4:45 p.m.
Chicago Cultural Center
78 E Washington St
North Shore Art League’s 12th Annual Art in the Village
Jun22
Festivals, Fairs & Special Events

North Shore Art League’s 12th Annual Art in the Village

Art in the Village, sponsored by the North Shore Art League will take place at Hubbard Woods Park (939 Green Bay Road) in Winnetka on…

Sunday, June 22nd
10:00 a.m.5:00 p.m.
939 Green Bay Rd, Winnetka
939 Green Bay Rd
Chicken Little at Chicago Kids Company
Jun22
Theatre & Performing Arts

Chicken Little at Chicago Kids Company

The Sky is Falling!  The Sky is Falling!  Join Chicken Little and her friends –Ducky Lucky, Goosey Loosey, Turkey Lurkey and others– as she journeys to tell…

Sunday, June 22nd
10:30 a.m.11:30 a.m.
Wilbur Wright College
4300 N. Narragansett Ave.
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Jun22
Tours & Attractions

The World Within: Chicago’s Original & Best Architecture Interiors Tour

“Everything has beauty, but not everyone sees it.”  (Confucius) Everyone does a boat tour when they visit Chicago.  But as fun as that is, it’s…

Sunday, June 22nd
11:00 a.m.1:00 p.m.
Chicago Loop & River North
Chicago Pride Fest 2025
Jun22
Festivals, Fairs & Special Events

Chicago Pride Fest 2025

Chicago Pride Fest® is a two-day street festival on June 21-22, 2025; the weekend before the Chicago Pride Parade (June 29, 2025). The 24th annual Chicago…

Sunday, June 22nd
11:00 a.m.8:00 p.m.
Northalsted
Halsted Street from Addison to Grace Streets
Chicago Greeter InstaGreeter Walks of the Riverwalk
Jun22

Chicago Greeter InstaGreeter Walks of the Riverwalk

Explore the Chicago Riverwalk with our knowledgeable volunteers! InstaGreeter walks take you on a free hour-long guided walk of the Riverwalk, without the need to…

Sunday, June 22nd
11:30 a.m.1:00 p.m.
Vietnam Veteran’s Memorial
Chicago Greeter InstaGreeter Walks of the Loop
Jun22

Chicago Greeter InstaGreeter Walks of the Loop

InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago’s top sights? Let InstaGreeter take you on a free hour-long guided…

Sunday, June 22nd
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Chicago Skyline Sail – Escape the City Hustle
Jun22
Tours & Attractions

Chicago Skyline Sail – Escape the City Hustle

Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…

Sunday, June 22nd
1:00 p.m.2:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
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