Various venues

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Kate McKinnon, Margaret Atwood, Salman Rushdie and Nick Offerman. You can see a full schedule of programming on the Chicago Humanities Festival website. 

Check out galleries and artistic spaces around Wicker Park and Bucktown during this free monthly event that takes place the first Friday of each month. Venues will keep their doors open until 8pm so guests can meet gallery owners and artists, and explore a range of local art. Participating spots include Jackson Junge Gallery, Tom Robinson Gallery, SoNa Contemporary Art, Torque Ltd., Prism Spaces and more.

A marquee program of the Chicago Cultural Alliance, Journey Chicago is a series of events taking place at cultural heritage centers across Chicagoland throughout October. Attendees can expect to experience unique cultural encounters, including Stitching Stories: Asia from East to West, Mid-Autumn Festival hosted by the Chinese American Museum of Chicago and Family Album Day, a genealogical experience presented in partnership by the Puerto Rican Arts Alliance and Bronzeville Historical Society. Check out the Journey Chicago website for the full calendar of events.

Want to get a free, behind-the-scenes look at the Chicago Board of Trade Building, Walt Disney's birthplace home, Orchestra Hall at Symphony Center and more iconic buildings throughout the Chicago area? You’ll have a chance to do so when the Chicago Architecture Center’s annual festival Open House Chicago returns to the city, opening up more than 170 architectural wonders across the city for free tours.