BEST Things to Do in Chicago This Weekend (September 25-27, 2026)

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.

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:

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

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

Hell in a Handbag Productions Presents Joan Crawford Goes To Hell at The Clutch – Extended through October 4, 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

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.