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.

All aboard! For the first time ever, the Chicagoland Independent Bookstore Alliance is bringing together 43 indie bookstores throughout Chicagoland for a special holiday shopping experience tailormade for all the book worms out there. With 10 routes to choose from, each trolley ride will include special holiday swag and stops at four to five participating bookstores. Variety abounds when it comes to this unique event: each route has a unique starting location (in Chicago and surrounding suburbs) and a unique duration.