Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (September 21-27, 2026) including the best events and activities.
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 Events This Week in Chicago
Below are the best events this week in Chicago:
Flotsam River Circus at the Chicago Riverwalk Theater – Monday, September 21, 2026, 6pm | Free (donations appreciated) – Troupe of musicians, circus performers and puppeteers who travel on a ramshackle raft giving free performances across the US.
Chicago Wellness Week – September 21-27, 2026 – Inaugural celebration of movement, mindfulness, and modern wellness.
Edison Park Restaurant Week – September 21-27, 2026
Chicago Gourmet – September 23-27, 2026
Chicago Underground Film Festival – September 23-27, 2026
St. Helen Carnival – September 24-27, 2026 | Free – Rides, music, food and family fun.
World Music Festival – September 25 – October 4, 2026 | Free Admission – Citywide including the Chicago Cultural Center
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)
Andersonville Arts Weekend – September 25-27, 2026
Sabor Fest – September 25-27, 2026 | Free ($5 suggested donation)
Oaktoberfest (Oak Park) – September 25-26, 2026
WNDR Museum Closing Party – Friday, September 25, 2026, 7-11:55pm
Beverly Art Walk – Saturday, September 26, 2026, 11am-5pm | Free
Rosetoberfest (Rosemont) – Saturday, September 26, 2026, 12-6pm
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.
Andersonville Fall Wine Walk – Sunday, September 27, 2026, 2-5pm
Twisted Tarot: Where Comedy Meets Fate and the Secrets of Tarot – Sunday, September 27, 2026, 4pm & 6:30pm
More Events in Chicago This Week
Below are more events taking place this week in Chicago:
Tango Dancing at Gallagher Way – Monday, September 21, 2026, 7-10pm | Free
Yoga Class at Gallagher Way – Tuesday, September 22, 2026, 7-8am | Free
Live Music in Space Park – Tuesday, September 22, 2026, 6-8pm | Free
Weezer The Gathering Tour at the United Center – Tuesday, September 22, 2026, 7pm
Sip and Paint at 360 Chicago – Tuesday, September 22, 2026, 7-8:30pm
HIIT at Gallagher Way – Wednesday, September 23, 2026, 7-8am | Free
Illinois Free Wednesdays at the Field Museum – Wednesday, September 23, 2026
Fall into Fitness: Pilates at Clarendon Park – Wednesday, September 23, 2026, 6-7pm | Free
Bottomless Margaritas on the Riverwalk (21+) – Wednesday, September 23, 2026, 6:30-9pm
Fall Equinox Bunny Yoga – Wednesday, September 23, 2026, 7:15-8:15pm
Yoga Class at Gallagher Way – Thursday, September 24, 2026, 7-8am | Free
Dance Fitness in Wicker Park – Thursday, September 24, 2026, 5:30-6:30pm | Free
Ciderfest: A Seasonal Cider Celebration at Artifact Events – Thursday, September 24, 2026, 6:30-9:30pm – One-night cider tasting experience featuring seasonal pours and fall flavors.
Kids Free Day at the Chicago Children’s Museum at Navy Pier – Friday, September 25, 2026, 10am-5pm | 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
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
You can find more Chicago weekend events here.
Free Days for Illinois Residents at Peggy Notebaert Nature Museum – September 21-25, 2026 | Free admission
Griffin Museum of Science and Industry Free Admission Days for Illinois Residents – September 20-23 & 27, 2026
Twin Peaks: Moving Through Time Film Series at the Music Box Theatre – Through September 22, 2026
Liliom at Lyric Opera House – Through September 27, 2026
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
Hell in a Handbag Productions Presents Joan Crawford Goes To Hell at The Clutch – Extended through October 4, 2026
Oktoberfest Nation (Fulton Market) – Through October 24, 2026
Jack’s Pumpkin Pop-up – Through November 1, 2026
More Things to Do in Chicago This Week
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 week 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.
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 week. 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 planning ahead, you can find more things to do in Chicago in September.
