Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (October 30 – November 1, 2026) including the best events and activities.
You can find more things to do in Chicago this week here.
(If you are planning ahead, you can also find the best things to do next weekend here.)
I suggest bookmarking this blog post as it is updated regularly with new events and activities.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Upside Down Parade – Saturday, October 31, 2026, 12pm–2pm | Free
Haunted Halsted Halloween Fest & Parade – Saturday, October 31, 2026 | Free – The Haunted Halsted Fest features food, drinks, live entertainment, street performers and dedicated areas/activities for kids and families throughout the day, leading right into the nightime Halloween Parade featuring a Costume Contest.
Homerathon at The National Hellenic Museum – October 29 & 30, 2026 | Free – Annual community reading of Homer’s The Odyssey aloud in its entirety. Visitors can sign up to read a three-minute passage.
Sanctum Dark Music Festival at Thalia Hall – October 30-31, 2026
4th Annual Halloween Vintage & Artisan Fest – October 31-November 1, 2026, 12-5pm
Family Field Night: Boo with SUE – Friday, October 30, 2026, 6-9pm
The Poetry Brothel Chicago: MONSTERS! – Friday, October 30, 2026, 7pm
Halloween Horror Film Classic: Nosferatu – Friday, October 30, 2026, 7-9:30pm – Silent black and white movie accompanied by live organ music.
Streeterville Doggy & Kitty Halloween Party at Museum of Contemporary Art Chicago – Saturday, October 31, 2026, 9-11am
Haunted House Party at Shedd Aquarium (21+) – Saturday, October 31, 2026, 7-11pm
The Jazz Room: This is Halloween Edition – Saturday, October 31, 2026, 6pm & 8pm
The Rocky Horror Picture Show – Original Cast Spooktacular at the Chicago Theatre – Saturday, October 31, 2026, 7:30pm
Haunted Halloween Ball at the Congress Plaza Hotel – Saturday, October 31, 2026, 9pm–2am
De Los Muertos at Navy Pier – Sunday, November 1, 2026, 1-5pm | Free – Art, cultural experiences and activities.
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Movies in the Parks: Hocus Pocus at Athletic Field Park – Friday, October 30, 2026, 5:30-8pm | Free
Barrio Bugalú – Halloween Edition Feat DJ Pablo Yglesias at the Segundo Ruiz Belvis Cultural Center – Friday, October 30, 2026, 6-9:30pm
MEMENTO MORI Halloween Gala at the International Museum of Surgical Science (21+) – Friday, October 30, 2026, 7-11pm
Carrera de los Muertos / Race of the Dead (Pilsen) – Saturday, October 31, 2026, 8am
Legendary Late Hours at the Field Museum – Saturday, October 31, 2026, 9am-9pm
Island Party Hut Fall Fest on the Riverwalk – Saturday, October 31, 2026, 12-8pm
Slightly Spooky Saturday at Navy Pier – Saturday, October 31, 2026, 1-8pm | Free
Nightmare on Wacker Drive: Dia De Los Muertos at LondonHouse – Saturday, October 31, 2026, 9pm-1am
Hot Chocolate Run – Sunday, November 1, 2026, 7:30am
Día de Los Muertos Workshops & Ofrenda Walk at Steelworkers Park – Sunday, November 1, 2026, 10am-1pm | Free
Kids Free Day at Chicago Children’s Museum – Sunday, November 1, 2026, 10am-5pm
Music Box of Horrors: The Final Chapter Film Series – Through October 31, 2026
The Rocky Horror Picture Show: Halloween Edition! at the Music Box Theatre – October 28 – November 1, 2026
Fright at the Field – Through November 1, 2026
Lincoln Park Zoo Fall Fest – Through November 1, 2026
Jack’s Pumpkin Pop-up – Through November 1, 2026
A Midsummer Night Scream at Greenhouse Theater Center – Through November 1, 2026
The Book of Mormon at Cadillac Palace Theatre – Through November 1, 2026
Don Giovanni at the Lyric Opera House – Through November 1, 2026
More Things to Do in Chicago This Weekend
Visit a Pumpkin Patch
This is the last weekend to visit pumpkin patches and farms in the Chicago area before they close for the season. Here is a list of the best pumpkin patches in and near Chicago.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this weekend include:
Halloween Classics
Tribute to Phil Collins
Tribute to Juan Gabriel on Strings
You can find the full list of candlelight concerts in Chicago here.
AirOtic BITE
AirOtic BITE is a dark and seductive Halloween burlesque and contemporary circus experience that is ending its limited time run this weekend. 21+ with valid ID.
When: Through November 1, 2026
Where: Experience 868, 868 N Franklin St, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Drunk Dracula
Step into a darkly enchanting adult-only adventure at Drunk Dracula where laughter, tipsy thrills, and the legend of Dracula collide. Each 90-minute session invites you to sip, shiver, and revel in the mischievous antics of a vampire gone delightfully rogue. Mingle with fellow thrill-seekers in a mysterious, adult-only setting. Must be 21+ with valid ID.
When: Through November 7, 2026
Where: 182 North Wabash Avenue, Chicago, IL 60601
Cost: Prices start at $29 per person. Click here to purchase tickets.
Serial Killer: The Exhibition World Tour
Serial Killer: The Exhibition World Tour is a gripping, immersive true-crime experience featuring the world’s first and only collection of authentic artifacts connected to history’s most notorious serial killers. Following its massive success in London, Paris, and Berlin, and fresh off its U.S. premiere in Atlanta, Chicago is officially the second stop of this blockbuster American tour. Built on ten years of research and collaboration with over sixty global collectors, this expanded landmark exhibition features over 2,100 authentic artifacts while introducing exclusive Chicago content exploring the city’s dark criminal history, including dedicated sections on H.H. Holmes and John Wayne Gacy. Recommended for ages 14+ (not suitable for sensitive audiences).
Where: Cinespace Chicago Film Studios, 2428 W 15th St, Chicago, IL 60608
Cost: Prices vary. Click here to purchase tickets.
Wondra: Immerse yourself in the magic of nature
Looking for a fun activity for kids? Head to the suburbs for Wondra, where each space invites curious minds to discover hidden details, dazzling colors, and natural awe-scapes that spark imagination and evoke wonder. Experience nature’s wonders in a whole new light with this immersive journey.
When: Through November 6, 2026
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets.
Take a Ghost Tour
Explore Chicago while learning about its haunted past. Visit the sites of some of the most gruesome disasters and murders in Chicago’s history while hearing stories of death, disaster, murder, ghosts, and infamous gangsters from your local guide.
Join this haunted segway tour or Halloween bike tour.
This ghosts and gangsters tour covers Chicago’s history of organized crime.
Watch Scary or Spooky Movies on a Rooftop
Rooftop Cinema Club will be showing classic horror movies and Halloween themed movies this week both for adults and families. Rooftop Cinema Club is an outdoor screening series on a rooftop located on the fifth floor terrace of The Emily Hotel in Fulton Market. The high end movie experience has state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks.
Address: The Emily Hotel (311 N Morgan St)
Cost: Prices vary. You can see prices and purchase tickets in advance here.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
As you can see there are many things to do in Chicago this weekend. If you are looking for things to do during the week, you can find more things to do in Chicago in October here and November here.
