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The Best Things To Do in Chicago This September

Summer is ending but the fun doesn’t have to stop in CHI. ☀️💃

by Chicago Bucket List


Spend the last few weeks of summer soaking up the sun, music, art, and food around Chicago! From limited edition Banksy pieces to live jazz, the summer adventure isn’t over just yet. Here are the best things to do in Chicago this September. 

The Art of Banksy Exhibit 

The Art of Banksy holds the world’s largest collection of privately owned Banksy art! On display are prints, canvasses, screenprints, sculptures, and  many limited-edition pieces from 1997 to 2008. 

Where: 360 N. State St, Chicago, IL 60654
When: Starting August 14th 

The Woman-ish Experience 

More than an exhibit, Womanish is a movement! Celebrate all things womanhood at this one-of-kind experience. There’s 40,000 square feet of immersive art, insta-worthy moments and thought-provoking interactive adventure. 

When: Thursday: 3 pm – 8 pm, Friday: 3 pm - 9 pm (last session at 9pm), Saturday: 11 am – 9 pm (last session at 9pm), Sunday: 11 am – 8 pm (last session at 8pm)
Where:114 S. State Street, Chicago, IL 60603

Catch A Drive-in Movie At ChiTown Drive-In  

Dinner and a movie just got better! Catch film classics like Grease from the comfort of your car at the drive-in theaters. Here, social distancing and safety measures are at the forefront of the fun. 

When: Varies. Follow @ChicagoBucketList for weekly movie schedule updates.
Where: 2343 S Throop St, Chicago, IL 60608 

Listen To Live Music At Pitchfork Music Festival 

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30+ artists from R&B to Electronic, Pitchfork has something for every music lover. Spread out over three days at Union Park, this is a perfect way to welcome the new season. 

When: September 10 - 12
Where: 1501 W Randolph St, Chicago, IL 60606

Watch Digital Projections At Art On theMart 

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The largest digital art projection in the world is in Chicago! Spend an evening Art On theMart to catch animations of famous artists like Frida Kahlo. 

When: Now - September 16 
Where: Best viewed on The Chicago Riverwalk between Wells and Lake St. 

Sonic Pavillon Festival 

Credit: Sonic Pavillon Festival 

Watch Millennium Park transform into an experimental sound haven at Sonic Pavillon. The festival is a series of 30 sound installations sure to immerse you in a canopy of sound.  

When: Now - September 30
Where: 201 E Randolph St, Chicago, IL 60602

Hyde Park Jazz Festival 




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From classic to contemporary, jazz lovers shouldn’t miss Hyde Park Jazz Festival this September. The free festival honors its roots with special jam sessions that mimic the 1960s and 70s jazz culture.   

When: September 25 - 26 
Where: Hyde Park 

Eat Tacos At Lakeview Taco Festival 

Credit: Chicago Events

A celebration for tacos with live music? Count us in! No matter how you prefer your tacos, Lakeview Taco has something for every taco lover--from chorizo to duck. 

When: September 18 - 19 
Where: 3500 N Southport Ave, Chicago, IL 60657