Castle
Oct2

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 2nd
10:00 a.m. – 5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
Flyway City: Architecture for a Flourishing Ecosystem
Oct2

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 2nd
10:00 a.m. – 5:00 p.m.
Chicago Architecture Center
111 E. Wacker Dr.
Mini Zoom Room
Oct2
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 2nd
10:00 a.m. – 5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct2
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 2nd
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Serial Killer: The Exhibition
Oct2
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 2nd
11:00 a.m. – 7:00 p.m.
Cinespace
1501 S Rockwell St
Chicago Greeter Riverwalk InstaGreeter Walk
Oct2

Chicago Greeter Riverwalk InstaGreeter Walk

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

Friday, October 2nd
11:30 a.m. – 1:00 p.m.
Vietnam Veteran’s Memorial
Marriott Theatre Presents Come From Away
Oct2
Theatre & Performing Arts

Marriott Theatre Presents Come From Away

Marriott Theatre, Chicagoland’s longest-running musical theatre presents Come From Away, the internationally celebrated musical that was nominated for seven Tony Awards, including Best Musical, captured four Laurence Olivier Awards,…

Friday, October 2nd
1:00 p.m. – 7:30 p.m.
Marriott Theatre
10 Marriott Drive
Chicago Greeter – Loop InstaGreeter
Oct2

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 2nd
1:30 p.m. – 3:00 p.m.
Chicago Cultural Center
78 E Washington St
Mäkelä Conducts Mahler 9
Oct2
Music & Comedy, Theatre & Performing Arts

Mäkelä Conducts Mahler 9

Mahler’s last completed work, the Ninth Symphony, opens with a sighing farewell, but that’s just the start. The composer takes you on a journey through…

Friday, October 2nd
1:30 p.m. – 3:30 p.m.

220 S. Michigan Ave.
DePaul Athletics Men’s Soccer
Oct2
Sports & Recreation

DePaul Athletics Men’s Soccer

  10/2: Friday 3PM vs Akron Big Vinny 25th Anniversary Celebration Join us as we celebrate the 25th anniversary of Big Vinny, the iconic mural…

Friday, October 2nd
3:00 p.m. – 5:00 p.m.
Wish Field
900 W Belden Ave
Shane
Oct2
Theatre & Performing Arts

Shane

In this World Premiere adaptation of the classic western, Shane, a mysterious stranger, shows up at the Starrett homestead in the Wyoming Territory in 1889.…

Friday, October 2nd
3:00 p.m. – 5:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
Lincoln Square Ravenswood Apple Fest 2026
Oct2
Festivals, Fairs & Special Events

Lincoln Square Ravenswood Apple Fest 2026

The 39th Annual Apple Fest runs on N. Lincoln Avenue between W. Lawrence and W. Sunnyside Avenues in Lincoln Square. Hours are Friday, October 2,…

Friday, October 2nd
3:00 p.m. – 6:00 p.m.
Giddings Plaza in Lincoln Square
4733 N Lincoln Ave, Chicago, IL 60625
City Cruises Chicago Seadog Haunted River Tour
Oct2
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 2nd
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
Oct2

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 2nd
4:00 p.m. – 6:00 p.m.
Inside Chicago Walking Tours
Starting location given upon ticket purchase
SAUCED Night Market
Oct2
Festivals, Fairs & Special Events

SAUCED Night Market

The south side of Chicago is about to get a little saucier. On Friday and Saturday, October 2 and 3 from 5 to 10 p.m. at HOSTE (1857…

Friday, October 2nd
5:00 p.m. – 10:00 p.m.
HOSTE
1857 W 16th St
Wicker Park Bucktown’s “First Fridays” Art Walk
Oct2

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 2nd
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
Oct2

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 2nd
6:00 p.m. – 8:00 p.m.
Intuit Art Museum
756 N Milwaukee Ave
FashionBar THE SHOWS: October 2026 – The Trans Media Fashion Show
Oct2
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

FashionBar THE SHOWS: October 2026 – The Trans Media Fashion Show

The Trans Media Fashion Show – October 2026 Date: Friday, October 2, 2026 Time: 6:00 PM – 9:00 PM Location: Water Tower Place – Level…

Friday, October 2nd
6:00 p.m. – 9:00 p.m.
WATER TOWER PLACE – Level 3, Michigan Ave.
Pandemonium, Please Hold
Oct2
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 2nd
6:30 p.m. – 8:00 p.m.
The Second City
1616 N. Wells St.
The Infinite Wrench
Oct2

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 2nd
7:00 p.m. – 8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
DaDA Reinvents the Wheel
Oct2
Music & Comedy

DaDA Reinvents the Wheel

Dada Reinvents the Wheel: An Interactive Comedy Experience Where Anything Can Happen Forget everything you know, except breathing—Dada Reinvents the Wheel is putting the fate…

Friday, October 2nd
7:00 p.m. – 8:00 p.m.
Stars & Garters
3914 N Clark St
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival
Oct2
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 2nd
7:00 p.m. – 8:15 p.m.
St. Agustine’s College
1345 W. Argyle St.
Reality Detox: The Improv Experience
Oct2

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 2nd
7:00 p.m. – 8:30 p.m.
The Second City
1616 N. Wells St.
Dauod Naimyar at The Comedy Bar
Oct2
Music & Comedy

Dauod Naimyar at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Dauood Naimyar taped a Comedy Central…

Friday, October 2nd
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611