Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (September 18-20, 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:
Riot Fest – September 18-20, 2026
Retro on Roscoe – September 18-20, 2026
The Magnificent Mile™ Art Festival – September 19-20, 2026 | Free
Lakeview East Festival of the Arts – September 19–20, 2026
Old Town Oktoberfest – September 18-20, 2026
Annunciation Cathedral Greek Fest – September 18-20, 2026 | Free Admission
Englewood Jazz Festival – September 17–19, 2026 | Free
Urban Birding Festival – September 18-20, 2026
Norwood Park Fall Fest – September 18-20, 2026
Chicago Live! Festival at Navy Pier – September 19-20, 2026 | Free
World Dumpling Fest – September 19-20, 2026
Flotsam River Circus at Ping Tom Park – September 16-17 & 19-20, 2026, 6pm | Free (donations appreciated) – Troupe of musicians, circus performers, and puppeteers who travel on a ramshackle raft giving free performances in waterfront towns across the US.
Oktoberfest at Guinness Open Gate Brewery – September 18-20, 2026
Oktoberfest at Brookfield Zoo – September 19-20, 2026, 10am-5pm
Chicago Exhibition Week – September 14–20, 2026
Reeling: Chicago LGBTQ+ International Film Festival – September 17–27, 2026
Rhinoceros Theater Festival – September 20-28, 2026 – Chicago’s longest-running fringe theater event.
All You Can Eataly: Septemberfest – Friday, September 18, 2026, 7-11pm
Chicago Story Fest – Friday, September 18, 2026, 8pm – Live show featuring award-winning journalists, writers, locals and comedians; short film and dance; live music and performance.
Island Party Hut Fall Fest on the Riverwalk – Saturday, September 19, 2026, 12-8pm – Every Saturday until Halloween.
Summer’s Last Dance Music & Arts Festival (Bridgeview) – Saturday, September 19, 2026, 1-11pm
Uptown Rhythm Festival – Saturday, September 19, 2026, 2-7pm | Free
Chicago’s Theatre of Magic at the Palmer House – Saturday, September 19, 2026, 4:30pm & 7:30pm
80s vs 90s Night at the Zoo – An Adults Only Evening at Lincoln Park Zoo – Saturday, September 19, 2026, 6:30-10pm
DANK Haus Oktoberfest Celebration – Saturday, September 19, 2026, 6:30-11:30pm
Ritmo del Mar at the Shedd Aquarium (21+) – Saturday, September 19, 2026, 7-11pm
Chicago River Swim – Sunday, September 20, 2026, 7-10am
Oktoberfest Nation – September 17 – October 24, 2026
Drunk Dracula – September 17 – November 7, 2026
Jack’s Pumpkin Pop-up – September 19 – November 1, 2026
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Dance Cardio and Sculpt at Gallagher Way – Friday, September 18, 2026, 7-8am | Free
Big Jump in Chicago River – Friday, September 18, 2026, 10am – Olympians, elected officials, civic leaders, celebrities, philanthropists and the public will take the plunge into the river while raising funds for ALS research and youth swim education.
Bronzeville Art District Trolley Tour – Friday, September 18, 2026, 6-9pm | Free
Third Friday Art Walk @ Zhou B Art Center – Friday, September 18, 2026, 7pm | Free
Open Studios (3rd Fridays) at Bridgeport Art Center – Friday, September 18, 2026, 7-10pm | Free
Lakewood Balmoral Yard Sale – Saturday, September 19, 2026, 9am-4pm
Bottomless Mimosas on the Riverwalk (Ages 21+) – Saturday, September 19, 2026, 11am-1pm
West Loop Wellness Fest – Saturday, September 19, 2026, 11am-2pm
Broadway in your Backyard at Navy Pier – Saturday, September 19, 2026, 12:30pm | Free
Reggaeton Beach Fest on Oak Street Beach – Saturday, September 19, 2026, 3-9pm
Tropical Cocktail Fest on North Ave. Beach – Saturday, September 19, 2026, 6-9pm
The Great Big Book Swap at American Writers Museum – Sunday, September 20, 2026, 10am-5pm | Free
Clink & Sip Festival – Sunday, September 20, 2026, 3-8pm
Phoebe Bridgers’ ‘The Lost Tour’ at the United Center – September 18 & 19, 2026, 7:30pm
Twin Peaks: Moving Through Time Film Series at Music Box Theatre – September 18-22, 2026
Liliom at Lyric Opera House – September 17-27, 2026
Willem de Kooning Drawing Exhibition at the Art Institute of Chicago – Through September 20, 2026
Dirty Dancing: The Musical at James M. Nederlander Theatre – Through September 20, 2026
More Things to Do in Chicago This Weekend
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 Adele
Tribute to TOOL
The Best of Hans Zimmer
Tribute to Juan Gabriel on Strings
You can find the full list of candlelight concerts in Chicago here.
Titanic: A Voyage Through Time
Step into history at Titanic: A Voyage Through Time an extraordinary virtual reality (VR) journey into history’s most famous ship. Dive to the wreckage as it rests today, then travel back to 1912 to experience the Titanic as a passenger. Walk the Grand Staircase, meet the people who shaped its story, and witness history firsthand in this immersive adventure.
When: Through September 27, 2026
Where: 108 West Germania Place, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
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.
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 September.
