Fri-Sat 5-6
Cry those end-of-summer tears into a wine glass at the Windy City Wine Festival in Grant Park. An entry ticket buys ten pours, so choose wisely from the 250 wines on offer (or just buy additional tasting tickets). It’s no secret that cooking demos (from the Hearty Boys) and talks from sustainable producers (like Bonterra) are more fun when you’re wasted. $25–$30. Daley Bicentennial Plaza, 337 E Randolph St (windycitywinefestival.com).

Sat-Sun 6-7
If you do one totally bizarre and awesome thing this week, head down to the Far South Side on Sunday for a free helping of Chicago’s largest pot of mulligan stew at the Historic Pullman Hobo Gathering. Stick around for exhibits, hobo entertainers and a barn dance. Don’t know what goes into mulligan stew? Neither does anyone else. Free. Arcade Park, 111th Pl and St. Lawrence Ave (hobofest.southchicago.info).

Sun 7
Is it bad to admit that pigging out at the Chicago Luxury Chocolate Salon sounds a lot more appealing than the types of philosophical debates that used to take place at traditional “salons”? Savor samples from chocolatiers like Mayana Chocolate or hit the chocolate liqueur instead. $20. 11am–5pm. Symphony Center, 220 S Michigan Ave (chicagochocolatesalon.com).