Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (September 14-20, 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 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.
Lincoln Park Uncorked Wine Stroll – Thursday, September 17, 2026, 6-9pm
Fall Wine Wobble Wicker Park Edition – Thursday, September 17, 2026, 6-9pm
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
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
Twin Peaks: Moving Through Time Film Series at Music Box Theatre – September 18-22, 2026
Rhinoceros Theater Festival – September 20-28, 2026 – Chicago’s longest-running fringe theater event.
Oktoberfest Nation Chicago (Fulton Market) – September 17 – October 24, 2026
Jack’s Pumpkin Pop-up – September 19 – November 1, 2026
Drunk Dracula – September 17- November 7, 2026
All You Can Eataly: Septemberfest – Friday, September 18, 2026, 7-11pm
Chicago Story Fest – Friday, September 18, 2026, 8pm – A 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
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
DANK Haus Oktoberfest Celebration – Saturday, September 19, 2026, 6:30-11:30pm
80s vs 90s Night at the Zoo – An Adults Only Evening at Lincoln Park Zoo – Saturday, September 19, 2026, 6:30-10pm
Ritmo del Mar at the Shedd Aquarium (21+) – Saturday, September 19, 2026, 7-11pm
Chicago River Swim – Sunday, September 20, 2026, 7-10am
More Events in Chicago This Week
Below are more events taking place this week in Chicago:
Pilates at Gallagher Way – Monday, September 14, 2026, 7-8am | Free
Yoga Class at Gallagher Way – Tuesday, September 15, 2026, 7-8am | Free
Sound Meditation at the Harold Washington Library – Tuesday, September 15, 2026, 5:30-7pm | Free
Live Music in Space Park – Tuesday, September 15, 2026, 6-8pm | Free
HIIT at Gallagher Way – Wednesday, September 16, 2026, 7-8am | Free
Illinois Free Wednesdays at the Field Museum – Wednesday, September 16, 2026
Bottomless Margaritas on the Riverwalk (Ages 21+) – Wednesday, September 16, 2026, 6:30-9pm
CatJam Chicago Jam Session at The Wild Mile – Wednesday, September 16, 2026, 7-10pm | Free
Art Institute of Chicago Free Hours for Illinois Residents – Thursday, September 17, 2026, 5–8pm | Free – Final Thursday of Free Summer Thursdays.
Growing Hope Concert at Gallagher Way – Thursday, September 17, 2026, 6-8pm | Free
Wild Mile Projections: Spectral Currents – Thursday, September 17, 2026, 8-8:30pm | Free
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 the Beach – Cocktail Tasting at 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
You can find more Chicago weekend events here.
Adler Planetarium Free Day (Illinois Resident Discount Days) – September 14-16, 2026
Free Days for Illinois Residents at Peggy Notebaert Nature Museum – September 14-18, 2026 | Free admission
Griffin Museum of Science and Industry Free Admission Days for Illinois Residents – September 15, 16 & 20, 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
Sunday in the Park with George – Through November 1, 2026
Jekyll & Hyde at Broadway Playhouse At Water Tower Place – Through November 8, 2026
More Things to Do in Chicago This Week
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 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 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.
