Castle
Oct23

Castle

Don your armor, pull out your spellbooks, and straighten your crown; Castle, presented by Shriners Children’s, is coming back to Chicago Children’s Museum. In this…

Friday, October 23rd
10:00 a.m. – 5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
Flyway City: Architecture for a Flourishing Ecosystem
Oct23

Flyway City: Architecture for a Flourishing Ecosystem

Flyway City: Architecture for a Flourishing Ecosystem, designed and co-curated by architecture and urban design practice Studio Gang in collaboration with the Chicago Architecture Center,…

Friday, October 23rd
10:00 a.m. – 5:00 p.m.
Chicago Architecture Center
111 E. Wacker Dr.
Mini Zoom Room
Oct23
Museums, Galleries & Exhibitions

Mini Zoom Room

A mini version of the beloved Zoom Room exhibit will be set up in the museum’s Great Hall for a limited time. On display and ready…

Friday, October 23rd
10:00 a.m. – 5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
BOO! at the Zoo
Oct23
Festivals, Fairs & Special Events

BOO! at the Zoo

Get ready for a boo-tiful day of Halloween fun at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly fall tradition! Enjoy festive décor, not-so-scary surprises,…

Friday, October 23rd
10:00 a.m. – 6:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct23
Festivals, Fairs & Special Events

INCREDIBLE INSECTS: Interactive Live Bug Exhibit

This Halloween season, join us for the third year of Incredible Insects at The Butterfly House at Navy Pier: an interactive exhibit featuring wacky and…

Friday, October 23rd
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Pigmented: Chicago to the World, A Black Fine Art Convening
Oct23
Museums, Galleries & Exhibitions

Pigmented: Chicago to the World, A Black Fine Art Convening

Pigmented: Chicago to the World is a national convening that celebrates Chicago’s unparalleled influence on Black visual art, design, sculpture, architecture, fabrication, scholarship, and cultural leadership. Presented…

Friday, October 23rd
11:00 a.m. – 5:00 p.m.
Logan Center for the Arts
915 E 60th St,
Emma Stebbins: Carving out History at Driehaus Museum
Oct23
Museums, Galleries & Exhibitions

Emma Stebbins: Carving out History at Driehaus Museum

Emma Stebbins: Carving Out History examines the full scope of Stebbins’s history‑making career as one of the most significant American sculptors of the nineteenth century. From…

Friday, October 23rd
11:00 a.m. – 5:00 p.m.
Driehaus Museum
40 E Erie St
Serial Killer: The Exhibition
Oct23
Museums, Galleries & Exhibitions, Tours & Attractions

Serial Killer: The Exhibition

Serial Killer: The Exhibition makes its Chicago debut on September 5, 2026, at Cinespace Film Studios Chicago, bringing the world’s largest private collection of authentic serial killer artifacts to…

Friday, October 23rd
11:00 a.m. – 7:00 p.m.
Cinespace
1501 S Rockwell St
Pilsen Día de Los Muertos Window Walk
Oct23
Museums, Galleries & Exhibitions

Pilsen Día de Los Muertos Window Walk

Día de Los Muertos Window Walk The Pilsen Chamber of Commerce is excited to welcome you to Pilsen’s 18th Street commercial corridor to marvel at…

Friday, October 23rd
12:00 p.m. – 11:30 p.m.
18th Street commercial corridor
West 18th Street, between Damen Ave and Halsted St.
Chicago Greeter – Loop InstaGreeter
Oct23

Chicago Greeter – Loop InstaGreeter

If you’re looking for a fast, flexible Greeter experience, check out our InstaGreeter walks. These hour-long guided walks are a fun and informal way to…

Friday, October 23rd
1:30 p.m. – 3:00 p.m.
Chicago Cultural Center
78 E Washington St
City Cruises Chicago Seadog Haunted River Tour
Oct23
Tours & Attractions

City Cruises Chicago Seadog Haunted River Tour

As Halloween season arrives, the Seadog Haunted River Tour returns to the Chicago River, offering guests a hauntingly fun journey through the city’s storied past.…

Friday, October 23rd
3:00 p.m. – 7:00 p.m.
City Cruises Chicago – Navy Pier
600 E Grand Ave
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Oct23

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

“Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime” is a 2-hour afternoon/evening walking tour that uncovers Chicago’s shadowy past through chilling tales…

Friday, October 23rd
4:00 p.m. – 6:00 p.m.
Inside Chicago Walking Tours
Starting location given upon ticket purchase
Wicker Park Bucktown’s “First Fridays” Art Walk
Oct23

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, October 23rd
6:00 p.m. – 8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Cutting and Pasting a World: The Paper Craft of Henry Darger
Oct23

Cutting and Pasting a World: The Paper Craft of Henry Darger

Intuit Art Museum (IAM), recognized worldwide as one of the few institutions dedicated solely to championing the work of self-taught artists, marks the 250th anniversary…

Friday, October 23rd
6:00 p.m. – 8:00 p.m.
Intuit Art Museum
756 N Milwaukee Ave
Virgil Marion Gallery’s Inaugural Exhibition Opening
Oct23
Museums, Galleries & Exhibitions

Virgil Marion Gallery’s Inaugural Exhibition Opening

Virgil Marion Gallery presents “Give Them Their Flowers” as its inaugural exhibition. An opening reception will take place Friday, October 23 from 6 – 9…

Friday, October 23rd
6:00 p.m. – 9:00 p.m.
2003 West Fulton Street, Suite 402
2003 West Fulton Street, Suite 402
Pandemonium, Please Hold
Oct23
Music & Comedy, Theatre & Performing Arts

Pandemonium, Please Hold

The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…

Friday, October 23rd
6:30 p.m. – 8:00 p.m.
The Second City
1616 N. Wells St.
Zoo Brews: Howls and Growls
Oct23
Festivals, Fairs & Special Events

Zoo Brews: Howls and Growls

Come for the brews, stay for the boos! Zoo Brews: Howls and Growls is an adults-only Halloween party at Lincoln Park Zoo that lets you…

Friday, October 23rd
6:30 p.m. – 10:00 p.m.
The Infinite Wrench
Oct23

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Friday, October 23rd
7:00 p.m. – 8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival
Oct23
Theatre & Performing Arts

El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival

This production is produced by Repertorio Latino TC and Colectivo El Pozo, written by Raúl Dorantes and directed by Joaquín Catana and Roma Díaz.  El…

Friday, October 23rd
7:00 p.m. – 8:15 p.m.
St. Agustine’s College
1345 W. Argyle St.
Reality Detox: The Improv Experience
Oct23

Reality Detox: The Improv Experience

Reality Detox: The Improv Experience is a high-energy night of improvisation from The Second City, with a few sketch surprises mixed in along the way. Built…

Friday, October 23rd
7:00 p.m. – 8:30 p.m.
The Second City
1616 N. Wells St.
Chicago Blackhawks vs. Montreal Canadiens
Oct23
Friday, October 23rd
7:00 p.m. – 8:30 p.m.
United Center
1901 W. Madison Street, Chicago
Zar the Star at The Comedy Bar
Oct23
Music & Comedy

Zar the Star at The Comedy Bar

Zar the Star is a New York City-based stand-up comedian and content creator whose sharp wit, bold storytelling, and unfiltered takes have made her one…

Friday, October 23rd
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Randy Feltface – Gimmick Tour
Oct23
Music & Comedy

Randy Feltface – Gimmick Tour

Australian comedian Randy Feltface is scheduled to perform in Chicago on Friday, October 23, 2026, as part of his “Gimmick” tour.

Friday, October 23rd
7:00 p.m. – 9:00 p.m.
The Vic Theatre
3145 N. Sheffield
Adam Ray – Chicago – Who Is Me Tour
Oct23
Music & Comedy

Adam Ray – Chicago – Who Is Me Tour

Comedian and actor Adam Ray will perform live in Chicago on Friday, October 23, 2026, at 7:00 PM. The performance is a headlining stop on…

Friday, October 23rd
7:00 p.m. – 9:00 p.m.
Historic Main Stage at Athenaeum Center
2936 N. Southport Ave