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 the fest’s biggest speakers this season include former Supreme Court Justice Stephen Breyer, architect Jeanne Gang, musician Kathleen Hanna and comedian Reggie Watts. You can see a full schedule of programming on the Chicago Humanities Festival website.

Now in its 19th year, the Andersonville Wine Walk, which benefits the Andersonville Chamber of Commerce, sees businesses throughout the neighborhood turn into wine destinations. You'll be able to sip, tour and shop your way through two wine routes curated by In Fine Spirits. Attendees will receive a commemorative wine tasting glass and a card highlighting each wine before embarking.

Curious Theatre Branch's Rhinoceros Theatre Festival, which bills itself as Chicago's longest-running fringe festival, returns for its 35th outing with a slate of new theater, music performances, art and more. Visit rhinofest.com for the complete schedule.