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Upcoming Chicago Events

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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.
Franz West: Millennium Park
Jun15
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 15th
Millennium Park
201 E Randolph St
Puerto Rican Festival Chicago 2025
Jun15

Puerto Rican Festival Chicago 2025

The Puerto Rican Festival Chicago 2025 returns for another exciting year JUNE 12-15, 2025, bringing together the community for a vibrant celebration of Puerto Rican heritage.…

Sunday, June 15th
See Chicago Dance’s Chicago Dance Month Returns This June
Jun15
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 15th
Various locations
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
Seeing Connections: The Art of Richard Penn
Jun15
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 15th
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
Jun15
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 15th
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
Flight of Butterflies
Jun15
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 15th
10:00 a.m.4:00 p.m.
Tom Torluemke: LIVE! ON PAPER, 1987 – 2024
Jun15
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 15th
10:00 a.m.4:45 p.m.
Chicago Cultural Center
78 E Washington St
Big Bus Tours’ Hop-On, Hop-Off Tour
Jun15
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Sunday, June 15th
10:00 a.m.5:00 p.m.
Hokusai & Ukiyo-e: The Floating World, Artworks from the Chiossone Collection
Jun15
Museums, Galleries & Exhibitions

Hokusai & Ukiyo-e: The Floating World, Artworks from the Chiossone Collection

Hokusai & Ukiyo-e features 70 works and handcrafted objects by the masters of Japan’s Edo Period (1603-1868). The collection features 53 woodblock prints and original…

Sunday, June 15th
10:00 a.m.6:00 p.m.
McAninch Arts Center at the College of DuPage
425 Fawell Blvd
Old Town Art Fair
Jun15
Festivals, Fairs & Special Events

Old Town Art Fair

Established in 1948, the Old Town Art Fair is one of Chicago’s oldest juried art fairs and one of the first fine art fairs of…

Sunday, June 15th
10:00 a.m.6:00 p.m.
Old Town Triangle Center
1763 N. North Park Ave.
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Jun15
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 15th
11:00 a.m.1:00 p.m.
Chicago Loop & River North
Spirited Storytelling: A Morning of Cocktails and Conversation with Andrew Friedman + John’s Food & Wine
Jun15

Spirited Storytelling: A Morning of Cocktails and Conversation with Andrew Friedman + John’s Food & Wine

The Chicago Chefs & Owners behind John’s Food & Wine, Adam McFarland & Tom Rogers (Chicago Tribune: Best Chefs 2025), invite you to the neighborhood…

Sunday, June 15th
11:00 a.m.1:00 p.m.
John’s Food & Wine
3114 N Halsted Street
Chicago Greeter InstaGreeter Walks of the Riverwalk
Jun15

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 15th
11:30 a.m.1:00 p.m.
Vietnam Veteran’s Memorial
Chicago Greeter InstaGreeter Walks of the Loop
Jun15

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 15th
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Rooftop Brunch at Nobu Chicago
Jun15

Rooftop Brunch at Nobu Chicago

Nobu Chicago will host a special edition of their popular weekend brunch, bringing it to The Rooftop restaurant and lounge on the 11th floor of…

Sunday, June 15th
11:30 a.m.2:00 p.m.
Nobu Chicago Rooftop
155 N. Peoria Street
JBF Greens x Galit – 2025 Awards Weekend Brunch
Jun15

JBF Greens x Galit – 2025 Awards Weekend Brunch

Three-course Middle Eastern brunch with wine pairings and pastries, hosted by JBF Greens at Galit. Location: Galit, 2429 N Lincoln Ave, Chicago, IL 60614

Sunday, June 15th
12:00 p.m.2:30 p.m.
Galit
2429 N Lincoln Avenue
Angels in America, Part Two: Perestroika
Jun15
Theatre & Performing Arts

Angels in America, Part Two: Perestroika

Part Two of Tony Kushner’s two-part, Pulitzer Prize-winning expansive, poetic, and politically charged look at the ‘80s in America. In the midst of the AIDS…

Sunday, June 15th
12:00 p.m.3:00 p.m.
Windy City Playhouse
3014 W. Irving Park Rd.
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