Pandemonium, Please Hold
Oct18
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…

Sunday, October 18th
7:00 p.m. – 8:30 p.m.
The Second City
1616 N. Wells St.
Reality Detox: The Improv Experience
Oct18

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…

Sunday, October 18th
7:00 p.m. – 8:30 p.m.
The Second City
1616 N. Wells St.
Calimar White at The Comedy Bar
Oct18
Music & Comedy

Calimar White at The Comedy Bar

Originally from St. Petersburg, Florida & currently based in Atlanta, Calimar White (AKA Agent Ratliff) is a hilarious standup comic, actor, influencer & business owner.…

Sunday, October 18th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Lightly Toasted Standup Showcase
Oct18
Music & Comedy

Lightly Toasted Standup Showcase

Lightly Toasted is a standup showcase at The Home Comedy Theater in the Lakeview neighborhood of Chicago every third Sunday of the month featuring up…

Sunday, October 18th
7:00 p.m. – 9:00 p.m.
The Home Comedy Theater
2843 North Halsted Street
Jekyll& Hyde
Oct18
Theatre & Performing Arts

Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Sunday, October 18th
7:00 p.m. – 10:00 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Vape! The Grease Parody
Oct18
Music & Comedy, Theatre & Performing Arts

Vape! The Grease Parody

Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…

Sunday, October 18th
7:30 p.m. – 8:55 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Harold Night
Oct18
Music & Comedy

Harold Night

See the show that started it all, and experience the iO Theater’s groundbreaking, signature improv form: The Harold! This long-running, weekly improv tradition is double-headlined…

Sunday, October 18th
7:30 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Deep Schwa
Oct18
Music & Comedy

Deep Schwa

Chicago’s longest-running Harold team returns to iO to bring their unique blend of chaos and creativity to iO’s signature form The Harold melding games, songs, and scenes…

Sunday, October 18th
8:00 p.m. – 9:30 p.m.
iO Theater
1501 N. Kingsbury St.
The 11pm Show
Oct18
Oct19
Music & Comedy

The 11pm Show

Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…

Sunday, October 18th
11:00 p.m. – Monday, October 19th
12:00 a.m.
iO Theater
1501 N. Kingsbury St.
62nd Chicago International Film Festival
Oct19
Festivals, Fairs & Special Events

62nd Chicago International Film Festival

As the longest-running competitive film festival in North America, The Chicago International Film Festival brings more than 150 films from around the world to Chicago.…

Monday, October 19th
Multiple Locations
Dinos!
Oct19

Dinos!

Starting May 22, Dinos! are taking over Brookfield Zoo Chicago. Come face-to-face with life-size dinosaurs throughout the Zoo. Journey through a massive rib-cage tunnel, climb…

Monday, October 19th
Brookfield Zoo Chicago
3300 Golf Rd
NoMI Gallery | Everything is Bright. All Things are Beautiful.
Oct19

NoMI Gallery | Everything is Bright. All Things are Beautiful.

NoMI Gallery Presents: 萬物生輝 Everything is Bright. All Things are Beautiful. NoMI is proud to present a curated exhibition by contemporary artist Dwight Hwang, whose…

Monday, October 19th
NoMI
800 N. Michigan Ave
We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago
Oct19

We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago

The new public art exhibit We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago celebrates the 250th anniversary of the Declaration…

Monday, October 19th
Greektown Chicago
300 S. Halsted
Chicago By Night River & Lake
Oct19
Tours & Attractions

Chicago By Night River & Lake

Glide along the Chicago River and Lakefront as you’re dazzled by the sparkle of the city at night. Hear lively commentary as you feel the…

Monday, October 19th
Chicago’s First Lady Cruises
112 E Wacker Drive
Creepy Cruise
Oct19
Tours & Attractions

Creepy Cruise

From strange sightings to eerie haunts, mobsters and more, our latest nighttime tour takes you into Chicago’s shadowy past. Cruise along the Chicago River as…

Monday, October 19th
Chicago’s First Lady Cruises
112 E Wacker Drive
Fright at the Field
Oct19
Museums, Galleries & Exhibitions

Fright at the Field

Spooky season has arrived at the Field Museum! Join us for Fright at the Field, a Halloween experience featuring the return of Underground MISAdventure, and…

Monday, October 19th
The Field Museum
1400 S Lake Shore Dr,
America@250 – Now is the Time: Artists Go to Work
Oct19
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Theatre & Performing Arts

America@250 – Now is the Time: Artists Go to Work

On July 4, 2026, America turned 250 years old. To reckon with the 250th anniversary of the Declaration of Independence is to reckon with freedom…

Monday, October 19th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”
Oct19
Museums, Galleries & Exhibitions, Tours & Attractions

“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”

The Pulitzer Prizes and American Library Association are bringing Pulitzer on the Road to the Harold Washington Library Center this fall. Opening October 14, the…

Monday, October 19th
8:00 a.m. – 5:00 p.m.
Harold Washington Library Center
400 S. State Street
Created Equal: The Premises and Promises of the Declaration of Independence
Oct19
Museums, Galleries & Exhibitions

Created Equal: The Premises and Promises of the Declaration of Independence

The Declaration of Independence grounded the revolutionary right of a people to overthrow a government in the philosophical premise that “all men are created equal.”…

Monday, October 19th
9:00 a.m. – 4:45 p.m.
Special Collections Research Center Exhibition Gallery
1100 East 57th Street
Homeschool Days at PEPPA PIG World of Play Chicago
Oct19

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Monday, October 19th
10:00 a.m. – 5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
American Prophets: Writers, Religion, and Culture
Oct19
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Monday, October 19th
10:00 a.m. – 5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Tangible Sound: Arrival to a Higher Ground
Oct19

Tangible Sound: Arrival to a Higher Ground

Imagine walking inside the thunderous sound of a taiko drum or feeling enveloped by the sinuous sounds of a saxophone, cello, or bass. What if…

Monday, October 19th
10:00 a.m. – 5:00 p.m.
Chicago Cultural Center
78 E Washington St
Castle
Oct19

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…

Monday, October 19th
10:00 a.m. – 5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
Flyway City: Architecture for a Flourishing Ecosystem
Oct19

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,…

Monday, October 19th
10:00 a.m. – 5:00 p.m.
Chicago Architecture Center
111 E. Wacker Dr.