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Upcoming Chicago Events

Check out what's happening all around Chicago.

Best Of Annoyance Sketch
Oct25
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, October 25th
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
Oct25
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, October 25th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Franz West: Millennium Park
Oct26
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, October 26th
Millennium Park
201 E Randolph St
The Sound of Music
Oct26
Theatre & Performing Arts

The Sound of Music

For 65 years, THE SOUND OF MUSIC has been one of our “favorite things.” With its timeless story and irresistibly charming score, this Rodgers & Hammerstein classic…

Sunday, October 26th
James M. Nederlander Theatre
24 W. Randolph St.
Ear Taxi Festival
Oct26
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Sunday, October 26th
Pumpkin Lights & Playful Frights
Oct26
Museums, Galleries & Exhibitions

Pumpkin Lights & Playful Frights

Step into WNDR this October for a seasonal spectacle like never before. Celebrate fall fun at WNDR Museum next month where treats, surprises, entertainment and…

Sunday, October 26th
wndr museum
1130 W Monroe St.
Wolff’s Flea Market Opening Day
Oct26
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, October 26th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Glenwood Sunday Market in Rogers Park
Oct26
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, October 26th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
CSI | Materiality in Sculpture: A Dialogue Between Substance and Form
Oct26
Museums, Galleries & Exhibitions

CSI | Materiality in Sculpture: A Dialogue Between Substance and Form

Evanston Art Center 2025 Exhibition: CSI | Materiality in Sculpture: A Dialogue Between Substance and Form EXHIBITION DATES: September 27 – November 9, 2025 OPENING…

Sunday, October 26th
9:00 a.m.4:00 p.m.
Evanston Art Center
1717 Central St
The Forgotten Lives Project
Oct26
Museums, Galleries & Exhibitions

The Forgotten Lives Project

The Evanston Art Center (EAC) is excited to welcome the public to The Forgotten Lives Project   “I’m a digital collage artist and photographer and…

Sunday, October 26th
9:00 a.m.4:00 p.m.
Evanston Art Center
1717 Central St
Leo Lionni’s Frederick
Oct26
Theatre & Performing Arts

Leo Lionni’s Frederick

While other mice are gathering food for the winter, Frederick daydreams the summer away. But when fall weather comes, it is Frederick who has stored…

Sunday, October 26th
9:30 a.m.10:30 a.m.
Chicago Children’s Theatre
100 S Racine Ave
By A Thread: Nature’s Resilience
Oct26
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Sunday, October 26th
10:00 a.m.4:00 p.m.
Boo! at the Zoo
Oct26
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Sunday, October 26th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Big Bus Tours’ Hop-On, Hop-Off Tour
Oct26
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, October 26th
10:00 a.m.5:00 p.m.
Living in the Shade: Open Space and Public Housing
Oct26
Museums, Galleries & Exhibitions

Living in the Shade: Open Space and Public Housing

This exhibition at the National Public Housing Museum explores the role of open space—large lawns and tenant gardens, paved paths and play spaces, shady seating…

Sunday, October 26th
10:00 a.m.5:00 p.m.
National Public Housing Museum
919 S. Ada St.
Illinois Holocaust Museum presents Experience360
Oct26
Museums, Galleries & Exhibitions

Illinois Holocaust Museum presents Experience360

Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…

Sunday, October 26th
10:00 a.m.5:00 p.m.
Illinois Holocaust Museum presents Experience360
360 N State St
Woodland Creatures’ Halloween
Oct26
Theatre & Performing Arts

Woodland Creatures’ Halloween

Theater for Young Audiences @ Corn presents our newest show, perfect for young ones and the entire family! In Woodland Creatures’ Halloween, our friends are…

Sunday, October 26th
11:00 a.m.12:00 p.m.
Cornservatory
4210 N Lincoln Ave
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Oct26
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, October 26th
11:00 a.m.1:00 p.m.
Chicago Loop & River North
Chicago Greeter InstaGreeter Walks of the Loop
Oct26

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, October 26th
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Rappel In Northwest Chicago
Oct26
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, October 26th
12:00 p.m.3:00 p.m.
Westin Chicago Northwest
400 Park Blvd.
Seadog Architecture Tour on the Chicago River
Oct26
Tours & Attractions

Seadog Architecture Tour on the Chicago River

Soak in unobstructed views of Chicago’s world-famous architecture with an exciting 45-minute ride on our Seadog Chicago River Architecture Tour! Starting right on the Chicago…

Sunday, October 26th
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
ABLE presents Frankenstein
Oct26
Theatre & Performing Arts

ABLE presents Frankenstein

Following a sold-out run at Chicago Shakespeare Theater, A.B.L.E.—Artists Breaking Limits & Expectations is thrilled to bring our critically acclaimed adaptation of Frankenstein back to…

Sunday, October 26th
1:00 p.m.2:30 p.m.
Theater Wit
Spooktacular 2025 | Clark Street
Oct26
Festivals, Fairs & Special Events

Spooktacular 2025 | Clark Street

Grab your costumes and candy buckets – it’s time for another full weekend of trick-or-treating at Spooktacular in Lincoln Park.  Join the Lincoln Park Chamber…

Sunday, October 26th
1:00 p.m.4:00 p.m.
Lincoln Park
Clark Street, From Armitage to Diversey, Diversey from Lakeview to Orchard
EXP Presents Horizon of Khufu
Oct26
Tours & Attractions

EXP Presents Horizon of Khufu

Be among the first to experience EXP Rosemont, a brand-new 26,000-square-foot immersive destination blending art, science and technology through rotating world-class experiences. Opening its doors…

Sunday, October 26th
1:00 p.m.8:00 p.m.
EXP
9900 Berwyn Avenue
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