Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (September 25-27, 2026) including the best events and activities.
{If you are planning ahead, you can also find the best things to do next weekend here.)
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Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
World Music Festival – September 25 – October 4, 2026 | Free Admission – Citywide including the Chicago Cultural Center
Chicago Gourmet – September 23-27, 2026
St. Helen Carnival – September 24-27, 2026 | Free – Rides, music, food and family fun.
African/Caribbean Intl Fest of Life & Jerk, Seafood & Vegan Festival – September 25-27, 2026
Oktoberfest at St. Alphonsus – September 25-27, 2026
WingOut – September 26-27, 2026
Clark Street Live (new) – September 26-27, 2026, 11am-10pm | Free (suggested donation) – New music festival in Wrigleyville.
Randolph Street Market – September 26-27, 2026
Hyde Park Jazz Festival – September 26-27, 2026 | Free ($10 suggested donation)
Sabor Fest – September 25-27, 2026 | Free ($5 suggested donation)
Andersonville Arts Weekend – September 25-27, 2026
Oaktoberfest (Oak Park) – September 25-26, 2026
Armitage County Fair – September 26-27, 2026 | Free ($10 suggested donation) – Inaugural street fest on Armitage Ave from California to Humboldt.
Chicago Wellness Week – September 21-27, 2026 – Inaugural celebration of movement, mindfulness, and modern wellness.
Chicago Underground Film Festival – September 23-27, 2026
Edison Park Restaurant Week – September 21-27, 2026
Midnight Circus at Welles Park – September 25-27, 2026
WNDR Museum Closing Party – Friday, September 25, 2026, 7-11:55pm
Chicago Humanities Fall Festival Pilsen Day – September 26, 2026
Beverly Art Walk – Saturday, September 26, 2026, 11am-5pm | Free
Rosetoberfest (Rosemont) – Saturday, September 26, 2026, 12-6pm – Parkway Bank Park’s second annual Oktoberfest-inspired celebration.
Top Shelf Tequila and Whiskey Tasting Festival – Saturday, September 26, 2026, 2:30-6pm
East Lakeview Neighbors Oktoberfest – Saturday, September 26, 2026, 3:30-7:30pm
Meet Me on Milwaukee – Sunday, September 27, 2026, 10am-6pm – Milwaukee Ave will be closed to automobile traffic between the North/Damen Intersection and Ashland Ave and replaced by live music, outdoor dining, sidewalk sales and more for pedestrians to explore.
Twisted Tarot: Where Comedy Meets Fate and the Secrets of Tarot – Sunday, September 27, 2026, 4pm & 6:30pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Kids Free Day at the Chicago Children’s Museum at Navy Pier – Friday, September 25, 2026, 10am-5pm | Free
Museum Late Night at Swedish American Museum – Friday, September 25, 2026, 4-7pm | Free
Bubblespalooza Kids’ Music Fest & Block Party – Saturday, September 26, 2026, 10am-1pm | Free
Barktoberfest at Sheraton Grand Chicago Riverwalk – Saturday, September 26, 2026, 10am-2pm | Free
Hispanic Heritage Fest at Brookfield Zoo – Saturday, September 26, 2026, 10am-6pm
Bottomless Mimosas on the Riverwalk (21+) – Saturday, September 26, 2026, 11am-1pm
Island Party Hut Fall Fest on the Riverwalk – Saturday, September 26, 2026, 12-8pm
Beatdown Sound System’s Vibrations of Freedom at Tom (Ping) Memorial Park – Saturday, September 26, 2026, 1-7pm | Free
Mid-Autumn Festival in Set In Stone at Burnham Park – Saturday, September 26, 2026, 4:30-7:30pm | Free
Tsukimi Moon Viewing Festival at Jackson Park – Saturday, September 26, 2026, 8-11pm | Free
Sustainability Market – Sunday, September 27, 2026, 10am-4pm | Free
Reeling: LGBTQ+ International Film Festival – Through September 27, 2026
Rhinoceros Theater Festival – September 20 – October 29, 2026 – Chicago’s longest-running fringe theater festival.
Lincoln Park Zoo Fall Fest – September 25 – November 1, 2026
If You Give a Mouse a Cookie at Greenhouse Theater Center – September 26 – October 25, 2026
A Midsummer Night Scream at Greenhouse Theater Center – September 24 – November 1, 2026
More Things to Do in Chicago This Weekend
In addition to the weekend events listed above, below are more of the best 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: September 17- 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 Phil Collins
Neo-Soul Favorites ft. Songs by Prince, Childish Gambino & More
Tribute to The Beatles
You can find the full list of candlelight concerts in Chicago here.
Minecraft Experience: Villager Rescue
Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
Take a Spray Paint ‘n’ Sip Urban Art Workshop
Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.
Where: Studio W.I.P. – Uptown, 1047 W Lawrence Ave, Chicago, IL 60640
Cost: $45 per person for adults. 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.
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets in advance.
As you can see there are many things to do in #Chicago this weekend. If you are looking for more things to do in the Chicago area, you can find the best things to do in the suburbs here. If you are looking for things to do during the week, you can find more things to do in Chicago this week here and the best things to do in Chicago in September here.
