Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (October 16-18, 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:
Open House Chicago – October 17-18, 2026 | Free – Offers behind-the-scenes access to architecturally, historically and culturally significant sites across the city.
Chicago Fashion Week – Through October 18, 2026
Chicago International Film Festival – October 14–25, 2026
Fall Clothing Swap at Chicago Fair Trade Museum & Store – October 16-18, 2026
Lincoln Square Greektober Fest – October 17–18, 2026 | Free
Spooky Zoo at Lincoln Park Zoo – Saturday, October 17, 2026 | Free
BooPalooza and BarkPalooza – Saturday, October 17, 2026, 10am-2pm | Free
The Beer Garden at Gallagher Way – Saturday, October 17, 2026, 11am-7pm
Loop Arts Fest – Saturday, October 17, 2026, 12-6pm | Free
Wicker Park Bucktown Thrift Riot – Saturday, October 17, 2026, 1-5pm | Free
Slightly Spooky October at Navy Pier – Saturday, October 17, 2026, 1pm | Free – Spooky activities, games, crafts and more followed by movies in the evening.
Lincoln Roscoe Beer Stroll – Saturday, October 17, 2026, 3-6pm
Ballet of Lights: Sleeping Beauty in a Sparkling Show – Saturday, October 17, 2026, 4pm & 6:30pm
Rosehill Cemetery Crypt 5K Run/Walk – Saturday, October 17, 2026, 7pm
The Volunteer Fair (Wicker Park) – Sunday, October 18, 2028, 12-4pm | Free
Chicago Artisan Market (Fulton Market) – Sunday, October 18, 2026, 11am-5pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Hispanic Heritage Celebration at Humboldt Park – Friday, October 16, 2026, 5-9pm | Free
Paranormal Prom: An Undead ’80s Aerial Showcase – Friday, October 16, 2026, 6:30-8pm
Third Friday Art Walk @ Zhou B Art Center – Friday, October 16, 2026, 7pm
Open Studios (3rd Fridays) at Bridgeport Art Center – Friday, October 16, 2026, 7-10pm | Free
Fall Festival at North Park Village Nature Center Park – Saturday, October 17, 2026, 10am-2pm | Free
BRA Crawl: Benefiting Breast Cancer Research – Saturday, October 17, 2026, 12-5pm
Fall Fest on the Riverwalk – Saturday, October 17, 2026, 12-8pm
The Wellness Retreat at Northerly Island – Saturday, October 17, 2026, 1-7pm
BWild x Wicker Park Farmers Market Free S
Outdoor Yoga Series at Wicker Park – Sunday, October 18, 2026, 9-10am | Free
Free Day at the American Writers Museum – Sunday, October 18, 2026, 10am-5pm
Roscoe Village Halloween Block Party – Sunday, October 18, 2026, noon-6pm
Chicago Vintage Fest – October 17 & 18, 2026 | Free
Waitress at James M. Nederlander Theatre – October 13–18, 2026
Boo! at the Zoo (Brookfield Zoo) – Through October 25, 2026
Rhinoceros Theater Festival – Through October 29, 2026 – Chicago’s longest-running fringe theater festival.
Lincoln Park Zoo Fall Fest – Through November 1, 2026
Jack’s Pumpkin Pop-up – Through November 1, 2026
Odyssey Reimagined Exhibit at the National Hellenic Museum – Through December 31, 2026
More Things to Do in Chicago This Weekend
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.
AirOtic BITE
AirOtic BITE is a dark and seductive Halloween burlesque and contemporary circus experience taking place only for a few weeks this October. 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.
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:
Tribute to Metallica
Tribute to The Beatles
You can find the full list of candlelight concerts in Chicago here.
Smithsonian Starstruck: An Immersive Experience
Launching in Chicago, and created in collaboration with the Smithsonian Astrophysical Observatory, Smithsonian Starstruck: An Immersive Experience is a fully interactive, 3D virtual reality experience that takes visitors on a breathtaking journey through the cosmos, from dazzling galaxies to the edge of a black hole.
When: Through December 27, 2026
Where: 108 West Germania Place, Chicago, IL 60610
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.
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.
