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Upcoming Chicago Events

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Chicago Greeter InstaGreeter Walks of the Loop
Sep21

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, September 21st
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Rappel In Northwest Chicago
Sep21
Sports & Recreation, Tours & Attractions

Rappel In Northwest Chicago

Conquer your limits at 168 feet up and rappel down the Westin Chicago Northwest in Itasca Illinois. Professional equipment provided and no experience needed. Trained…

Sunday, September 21st
12:00 p.m.3:00 p.m.
Westin Chicago Northwest
400 Park Blvd.
West Loop Music & Art Fest
Sep21
Festivals, Fairs & Special Events

West Loop Music & Art Fest

The West Loop Music & Art Fest transforms Fulton Street into a dynamic, open-air gallery and music venue. Spanning 5 city blocks, this family-friendly festival…

Sunday, September 21st
12:00 p.m.10:00 p.m.
West Loop
Jerk, Seafood & Vegan Fest (JSVFest)
Sep21
Festivals, Fairs & Special Events

Jerk, Seafood & Vegan Fest (JSVFest)

The JSVFest, now in its 9th year, will serve up the best Caribbean jerk, grilled seafood, and plant-based cuisine with an island twist featuring the…

Sunday, September 21st
12:00 p.m.10:00 p.m.
Union Park
1500 West Washington Blvd
Chicago Skyline Sail – Escape the City Hustle
Sep21
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, September 21st
1:00 p.m.2:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Late Nite Catechism, the Comedy Legend, Returns
Sep21
Theatre & Performing Arts

Late Nite Catechism, the Comedy Legend, Returns

Call it Loretta Young meets Carol Burnett and Whoopi Goldberg. Late Nite Catechism is part catechism class, part stand-up routine. Written by Vicki Quade &…

Sunday, September 21st
1:00 p.m.3:00 p.m.
The iO Theater
1501 North Kingsbury Street
Chicago White Sox vs. San Diego Padres
Sep21
Sunday, September 21st
1:10 p.m.3:30 p.m.
Guaranteed Rate Field
333 W 35th St
Tom & Eliza
Sep21
Theatre & Performing Arts

Tom & Eliza

Tom & Eliza is a dual meditation on the choices we make (and those we don’t) in a world that spins relentlessly into the future. Performed…

Sunday, September 21st
2:00 p.m.3:10 p.m.
TUTA Theatre
4670 N. Manor Avenue
Big White Fog
Sep21
Theatre & Performing Arts

Big White Fog

Theodore Ward’s Big White Fog is the big shoulders on which A Raisin in the Sun stands. First completed in 1938, funded by the Federal Theatre Project, and influenced…

Sunday, September 21st
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Chicago Skyline Sail – Escape the City Hustle
Sep21
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, September 21st
3:00 p.m.4:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
The Book of Will
Sep21
Theatre & Performing Arts

The Book of Will

Without William Shakespeare, we wouldn’t have literary masterpieces like ROMEO AND JULIET. But without Henry Condell and John Heminges, we would have lost half of…

Sunday, September 21st
3:00 p.m.5:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
Gangsta Baby
Sep21
Theatre & Performing Arts

Gangsta Baby

The hit production from the London Pub Theatre scene – first production in the US Junior is a queer sex worker in Hastings suffering from…

Sunday, September 21st
3:00 p.m.5:00 p.m.
Open Space Arts
1411 W. Wilson Ave, Chicago, IL, 60640
Refracted Theatre Company Presents “Dream Hou$e”
Sep21
Theatre & Performing Arts

Refracted Theatre Company Presents “Dream Hou$e”

Award-winning Refracted Theatre Company presents Dream Hou$e, written by Eliana Pipes and directed by Laura Alcalá Baker, September 12 – October 18, at the Den…

Sunday, September 21st
3:00 p.m.5:30 p.m.
The Den Theatre
1331 N Milwaukee Ave
Taste of Evanston
Sep21
Festivals, Fairs & Special Events

Taste of Evanston

The Taste of Evanston is North Shore’s premier foodie celebration! This year’s 11th anniversary event will feature 40 of Evanston’s most cherished restaurants, breweries and…

Sunday, September 21st
3:00 p.m.6:00 p.m.
Charles Gates Dawes House
225 Greenwood St
90 Minute Architecture River Tour in Chicago
Sep21
Tours & Attractions

90 Minute Architecture River Tour in Chicago

Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…

Sunday, September 21st
5:00 p.m.7:00 p.m.
Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
White Rabbit, Red Rabbit
Sep21
Theatre & Performing Arts

White Rabbit, Red Rabbit

Forbidden to leave his country, playwright Nassim Soleimanpour distilled the experience of an entire generation in a wild, utterly original play. WHITE RABBIT RED RABBIT…

Sunday, September 21st
7:30 p.m.9:00 p.m.
TUTA Theatre
4670 N. Manor Avenue
Big Bus Tours’ Sunset Live Tour
Sep21
Tours & Attractions

Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…

Sunday, September 21st
7:30 p.m.9:15 p.m.
618 N Clark St.
618 N. Clark St
Mr. Wolf
Sep21
Theatre & Performing Arts

Mr. Wolf

14 years ago, the infant Theresa was stolen from her parents. Now, the precocious 15-year-old has been rescued, and quickly returned to a family that…

Sunday, September 21st
7:30 p.m.9:30 p.m.
Big White Fog
Sep21
Theatre & Performing Arts

Big White Fog

Theodore Ward’s Big White Fog is the big shoulders on which A Raisin in the Sun stands. First completed in 1938, funded by the Federal Theatre Project, and influenced…

Sunday, September 21st
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
The Annoyance Sketch Show: Late Stage Everything
Sep21
Music & Comedy, Theatre & Performing Arts

The Annoyance Sketch Show: Late Stage Everything

The trains are late, the apps are broken, the bees are dying, and the algorithm knows your deepest fears. So what do we do? We…

Sunday, September 21st
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Franz West: Millennium Park
Sep22
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…

Monday, September 22nd
Millennium Park
201 E Randolph St
Dungeons & Dragons: The Twenty-Sided Tavern
Sep22
Theatre & Performing Arts

Dungeons & Dragons: The Twenty-Sided Tavern

Direct from New York City, the tavern returns to Chicago with an all new production! The global phenomenon that is DUNGEONS & DRAGONS is now…

Monday, September 22nd
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
The Messi Experience Chicago
Sep22
Museums, Galleries & Exhibitions

The Messi Experience Chicago

The Messi Experience is an immersive and interactive multimedia exhibition inspired by the life and career of Lionel Messi. As part of its world tour,…

Monday, September 22nd
2367 W Logan Blvd Chicago, IL 60647
2367 W Logan Blvd
The Cellar Door: The Hilt Estate
Sep22
Festivals, Fairs & Special Events

The Cellar Door: The Hilt Estate

Just thirteen miles from the Pacific, The Hilt Estate lies at the rugged, windswept edge of the Sta. Rita Hills AVA, where challenging conditions shape wines of…

Monday, September 22nd
The Oakville Grill & Cellar
163 N Green St
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