Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (October 9-12, 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:
Oktoberfestiversary – October 10-11, 2026
Lincoln Park Wine Fest – October 9-11, 2026
Chicago Fashion Week – October 8-18, 2026
Chicago Art Fair – October 7-10, 2026 – Inaugural event at the Merchandise Mart.
Chicago Vampire Ball – Friday, October 9, 2026, 8pm
TenderFest at Navy Pier – Saturday, October 10, 2026, 11am-3pm – All-you-can-taste chicken tender festival.
Chicago Zine Fest – Saturday, October 10, 2026, 11am-4pm | Free
Lincoln Brunch Fest – Saturday, October 10, 2026, 10am-2pm | Free – Local restaurants will serve free samples of brunch items.
Mocktoberfest (Evanston) – Saturday, October 10, 2026, 12-4pm
Bowmanville Cat Tour – Saturday, October 10, 2026, 3-5pm | Free
Chicago Marathon – Sunday, October 11, 2026
Columbus Day Parade – Monday, October 12, 2026, 12pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Windy City Witch Fest – October 9-10, 2026
Jazz City at Clarendon Community Center Park – Friday, October 9, 2026, 6:30-8:30pm | Free
An Idiot’s Guide to Wine – Friday, October 9, 2026, 6pm & 8:30pm
Pumpkin Painting Party at Peggy Notebaert Nature Museum – Saturday, October 10, 2026, 10:30am-2pm – Family event.
Healing Arts Chicago: An Arts x Health x Wellness Summit – Saturday, October 10, 2026, 10:30am-4pm | Free
Harvest Hangout at Gallagher Way – Saturday, October 10, 2026, 11am-5pm
Fall Fest on the Riverwalk – Saturday, October 10, 2026, 12-8pm
Chicago Spritz Fest – Bubbly Cocktail Tasting at I|O Godfrey Rooftop – Saturday, October 10, 2026, 1-5pm
Chicago Latino Dance Festival at Humboldt Park – Sunday, October 11, 2026, 3-5pm | Free
The 3RUN2 2026 Post-Marathon Dance Party (21+) – Sunday, October 11, 2026, 8pm-1am
Olivia Rodrigo The Unraveled Tour at the United Center – October 11 & 12, 2026, 7pm
Chicago History Museum Free Day for Illinois Residents – Monday, October 12, 2026 | Free
Operation Mincemeat: A New Musical – Through October 11, 2026
If You Give a Mouse a Cookie at Greenhouse Theater Center – Through October 25, 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 27, 2026
More Things to Do in Chicago This Weekend
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Kayak in the River or Lake
A fun way to explore the city is to go kayaking in the Chicago River or Lake Michigan. You can rent a kayak in the Chicago River here and Ohio Street beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
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 1, 2026
Where: 182 North Wabash Avenue, Chicago, IL 60601
Cost: Prices start at $29 per person. 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 Ariana Grande
Vivaldi’s Four Seasons (Oak Park)
Neo-Soul Favorites ft. Songs by Prince, Childish Gambino & More
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.
