Trick or Treat on Southport
Oct26
Festivals, Fairs & Special Events

Trick or Treat on Southport

The Lakeview Roscoe Village Chamber of Commerce will host its annual Trick or Treat on Southport on Oct. 26 from 4 to 7 p.m. Families…

Monday, October 26th
4:00 p.m. – 7:00 p.m.
Southport from Roscoe to Grace
Southport from Roscoe to Grace
DETROIT ’67
Oct26
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

DETROIT ’67

Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running  through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…

Monday, October 26th
7:30 p.m. – 10:30 p.m.
eta Creative Arts Foundation
7558 S South Chicago Ave
America@250 – Now is the Time: Artists Go to Work
Oct27
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…

Tuesday, October 27th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct27
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…

Tuesday, October 27th
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Xfinity’s “Surviving Dead Zones” Event at Green Door Tavern
Oct27
Festivals, Fairs & Special Events

Xfinity’s “Surviving Dead Zones” Event at Green Door Tavern

Join Xfinity from 7-9pm on Tuesday, October 27 for Surviving Dead Zones, a Halloween night of treats (and a few tricks) for guests 21+ at…

Tuesday, October 27th
7:00 p.m. – 9:00 p.m.
The Green Door Tavern
678 N Orleans St
America@250 – Now is the Time: Artists Go to Work
Oct28
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…

Wednesday, October 28th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct28
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…

Wednesday, October 28th
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
America@250 – Now is the Time: Artists Go to Work
Oct29
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…

Thursday, October 29th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct29
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…

Thursday, October 29th
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Nature Night Out
Oct29
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Nature Night Out

Join us on Thursday, October 29, from 6:00 to 8:30 PM for an adults-only evening at the Peggy Notebaert Nature Museum. Enjoy refreshments while exploring…

Thursday, October 29th
6:00 p.m. – 8:30 p.m.
America@250 – Now is the Time: Artists Go to Work
Oct30
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…

Friday, October 30th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Fall Fest at Lincoln Park Zoo
Oct30
Festivals, Fairs & Special Events

Fall Fest at Lincoln Park Zoo

Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…

Friday, October 30th
8:00 a.m. – 5:00 p.m.
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct30
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 30th
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Haunted Halloween Cruises
Oct30
Festivals, Fairs & Special Events, Tours & Attractions

Haunted Halloween Cruises

ChicagoCruiseEvents.com is hosting a roster of various cruises for the upcoming Halloween season- 4 different options starting at $20/ticket. Dance and drink the night away…

Friday, October 30th
7:30 p.m. – 10:30 p.m.
Anita Dee II Boarding at Dusable Harbor , 200 North Breakwater Access, Chicago, United States
Anita Dee II Boarding at Dusable Harbor , 200 North Breakwater Access, Chicago, United States
DETROIT ’67
Oct30
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

DETROIT ’67

Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running  through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…

Friday, October 30th
7:30 p.m. – 10:30 p.m.
eta Creative Arts Foundation
7558 S South Chicago Ave
Haunted Halloween Cruises
Oct30
Oct31
Festivals, Fairs & Special Events, Tours & Attractions

Haunted Halloween Cruises

ChicagoCruiseEvents.com is hosting a roster of various cruises for the upcoming Halloween season- 4 different options starting at $20/ticket. Dance and drink the night away…

Friday, October 30th
8:00 p.m. – Saturday, October 31st
11:00 p.m.
Anita Dee II Boarding at Dusable Harbor , 200 North Breakwater Access, Chicago, United States
Anita Dee II Boarding at Dusable Harbor , 200 North Breakwater Access, Chicago, United States
America@250 – Now is the Time: Artists Go to Work
Oct31
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…

Saturday, October 31st
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Fall Fest at Lincoln Park Zoo
Oct31
Festivals, Fairs & Special Events

Fall Fest at Lincoln Park Zoo

Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…

Saturday, October 31st
8:00 a.m. – 5:00 p.m.
INCREDIBLE INSECTS: Interactive Live Bug Exhibit
Oct31
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…

Saturday, October 31st
10:00 a.m. – 6:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago
Oct31
Festivals, Fairs & Special Events

Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago

The Ritz-Carlton Chicago invites families and fairytale lovers to step into a modern Cinderella story with “Before Midnight: A Cinderella Tea Experience,” an enchanting afternoon…

Saturday, October 31st
11:00 a.m. – 3:00 p.m.
The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611
160 E Pearson St 12th Floor
Fright on Farragut
Oct31
Festivals, Fairs & Special Events

Fright on Farragut

On Saturday, October 31, Farragut transforms into the most haunted street in Andersonville! Join us from 11AM–4PM at Clark & Farragut to show off your…

Saturday, October 31st
11:00 a.m. – 4:00 p.m.
Clark & Farragut
Clark & Farragut
Howl-O-Ween Pet Costume Contest
Oct31
Festivals, Fairs & Special Events

Howl-O-Ween Pet Costume Contest

Plan your costumes, pack up your pets, and join us at Harry Caray’s Navy Pier for our annual Howl-O-Ween Pet Costume Contest benefiting PAWS Chicago!…

Saturday, October 31st
11:30 a.m. – 1:30 p.m.
Harry Caray’s Navy Pier
700 East Grand Avenue
Slightly Spooky October at Navy Pier
Oct31
Festivals, Fairs & Special Events

Slightly Spooky October at Navy Pier

Join us for free movies at Navy Pier in Crystal Gardens on Saturdays, October 17 and 24, plus trick-or-treating throughout the Pier on Halloween, October…

Saturday, October 31st
1:00 p.m. – 10:00 p.m.
DETROIT ’67
Oct31
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

DETROIT ’67

Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running  through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…

Saturday, October 31st
3:00 p.m. – 6:00 p.m.
eta Creative Arts Foundation
7558 S South Chicago Ave