1 The Bears’ pursuit of their first winning season since 2012 begins Sept. 9. Expect Mitch Trubisky and do-it-all RB Tarik Cohen to flourish under pass-happy new coach Matt Nagy.
2 A 1960s local collective of art weirdness gets its due when Hairy Who? opens Sept. 27 at the Art Institute of Chicago. Brace yourself for questions from your kids. (Hello, random detached genitalia.)
3 City Council reconvenes Sept. 20. Burning issue on the docket: Ameya Pawar’s proposal for a universal basic income. The pilot would give 1,000 families $500 a month, no strings.
4 Piano legend Ramsey Lewis plays his farewell show on Sept. 1 at the Chicago Jazz Festival. Not a jazz nerd? You’ll still recognize his riffs from “Hang On Sloopy.”