From orchard visits to neighborhood fests, fall is full of excuses to get outside and soak it all in. We’ve rounded up a few local happenings to add to your list.
Find Your Groove at Englewood Jazz Festival
Celebrate six decades of Chicago jazz at the Englewood Jazz Festival. The weekend honors the 60th anniversary of the Association for the Advancement of Creative Musicians (AACM) with commissioned works from Renée C. Baker, Adegoke Steve Colson, and Ernest Dawkins. Enjoy live sets that highlight innovation and tradition, from bold improvisations to smooth classics, all performed by Chicago’s leading jazz artists.
Date: September 19-20
Time: Fri 6PM-7PM; Sat 12PM-6PM
Cost: Free
Location: Hamilton Park & Cultural Center, 513 W. 72nd St.
More Info: englewoodjazzfestival.org
Join the Festivities at Oktoberfest with the Cubs
Raise a stein at the first-ever Oktoberfest with the Cubs in Wrigleyville. From Friday to Sunday, the Toyota Camry Lot transforms with beer tents, live music, DJs, and authentic Bavarian fare from local favorites like Schnitzel Platz. Families can enjoy a Kinderfest with crafts, rides, and balloon art, while adults compete in stein-holding contests or join the Dachshund parade. Bavarian attire encouraged!
Date: September 19-21
Time: Fri 4PM-10PM; Sat 11AM-10PM; Sun 12PM-7PM
Cost: $15+
Location: Toyota Camry Lot, 1126 W. Grace St.
More Info: mlb.com
Explore the West Loop Music & Art Fest
Browse over 100 local and national artists selling paintings, ceramics, textiles, and handmade goods, or stop by interactive workshops and family-friendly crafts. As night falls, the festival shifts gears with live music and DJs, food trucks serving everything from street tacos to ice-cold drinks.
Date: September 20-21
Time: Sat 1PM-10PM; Sun 1PM-9:30PM
Cost: Free
Location: Fulton Market District
More Info: wcachicago.org
Taste Your Way Through Jerk, Seafood & Vegan Fest
Enjoy jerk chicken, fresh seafood, and inventive vegan dishes from local vendors, paired with live music and family-friendly activities. With food, fun, and community spirit, the festival turns a love of flavor into a full-day experience.
Date: September 20-21
Time: 11AM-9:30PM
Cost: $10 Suggested Donation
Location: Union Park, 1501 W. Washington Blvd.
More Info: jsvfest.com
Discover Local Talent at Edgewater Artists in Motion
Edgewater Artists in Motion showcases local talent across visual arts, music, and performance. Explore galleries, outdoor installations, and live performances by bands like Still Il and School of Rock Andersonville. Local businesses complement the experience with food, drinks, and artisan goods.
Date: September 21
Time: 11AM-7PM
Cost: Free
Location: Colvin House Mansion, 5940 N. Sheridan
More Info: edgewaterartists.org
