Things to do in Chicago in September


September is one of my favorite months in Chicago. The stifling summer humidity dissipates, but the crippling winter cold is still a few months away. Days are warm and sunny and nights slowly begin to get chillier. Window fronts are decorated with the clothes of the upcoming season – colorful tights worn with tall boots, jackets, and scarves – and thoughts of pumpkin patches and apple picking spring to mind. If you’re planning a September visit, here are some things to do while you’re here.

September 1, 8, 15, 22, 29– Free admission at the Art Institute from 5pm to 8pm and free admission at the Peggy Notebaert Nature Museum all day

September 1-4 – Chicago Jazz Festival – longest running lakefront fest in Chicago

September 3, 4, 10, 11, 17, 18, 24, 25 – Free tours of Half Acre Beer Company at 1pm. RSVP required.

September 4, 11, 18, 25– DuSable Museum of African American History from noon – 5pm

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September 4, 11, 18, 25 Free for All. Free improv comedy shows at the Playground. Best of all, shows are BYOB.

September 6, 13, 20, 27 – Free admission at the Museum of Contemporary Art Chicago, with free tours on Tuesdays at 1pm, 2pm and 6pm.

September 9 – Pilsen 2nd Friday Artwalk. One of my favorite monthly events, the Artwalk is held at galleries in Pilsen, around 18th and Halsted. Free wine and cheese and great art make this is an excellent (and low-cost) night out. 6pm-10pm

September 9 – Windy City Wine Festival – wine, wine and more wine in Grant Park

September 10 and 11 – Lakeview East Festival of the Arts – art from artists all over the country lines Broadway for two days

September 10 and 11 – Renegade Craft Fair – shop for cool handmade arts and crafts and support local artisans

September 10 – 11
Taste of Wells Street – celebrating the Old Town neighborhood with food, drinks, music, and vendors

September 17 – 18 –
Chicago Latin Music Festival

September 23-25 Chicago Gourmet food and wine festival in Millennium Park

Photos by afloden, Plaubul Makina