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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 GraceFestivals, 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 AveFestivals, 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…
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 StatesFestivals, 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 StFestivals, 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…
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 StatesFestivals, 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…
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 StatesFestivals, 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.Peggy Notebaert Nature Museum
2430 N. Cannon Dr.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…
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…
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 StatesFestivals, 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 StatesFestivals, 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 AveFestivals, 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 StatesFestivals, 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…
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…
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 StatesFestivals, 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 FloorFestivals, 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 & FarragutFestivals, 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 AvenueFestivals, 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…
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

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