The Chicago Jazz festival runs from August 28-August 31. It's a free event with quality live musical performances, and talent coming in from around the world! It's located in Millennium Park, 201 E Randolph Street, Chicago, IL 60602. There is convenient parking in the Millennium Park garage.
The Bucktown 5k is a race that runs entirely on closed city streets. This family event celebrates the neighborhood, and it is held on Sunday, September 14 at 8am. The race starts off at 1621 West Wabansia (Wabansia and Marshfield).
Riot fest is a punk and rock festival in nearby Humboldt Park. It runs for three days, from September 12-14, and it is open to all ages (admission is actually free for kids 5 and under when accompanied by an adult). There are Carnival rides, wrestling, and bands such as Jane’s Addiction, The Flaming Lips, Weezer, and The Offspring (this year). You can find the full lineup here: http://chicago.riotfest.org/?sort=day.
Keep an eye out for Leah in the Dropkick Murphy's moshpit, and Monika at Gogol Bordello's show!
The Wicker park Bucktown Farmers Market goes on every Sunday from 8am – 2pm at 1425 N. Damen Avenue. You'll find meats, cheeses, baked goods, locally grown produce, flowers and more.
The Renegade Craft Fair is on September 7th + 8th. It is a DIY extravaganza with artists from across the U.S. selling their handmade wares. It’s Free, and there are workshops, DJs, good food, and installations. Be there, or be sad you aren't there!