October on the South Side brings music, film, neighborhood traditions, and a few can’t-miss community favorites. We’ve rounded up a handful of local events to help you plan the month.
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South Side Events for October 2026
Topdog/Underdog at Steppenwolf Theatre
Date: Friday, October 2 – November 1, 2026
Location: Steppenwolf Theatre, 1650 N. Halsted St. Chicago IL, 60614
Cost: Varies
Learn more about Topdog/Underdog here.
Cookies and Karaoke at Strugglebeard Bakery
Date: Friday October 2 & 9, 2026
Location: Strugglebeard Bakery, 5221 S. Harper Court
Learn more about Cookies and Karaoke at Strugglebeard Bakery here.
Cookies & Culture Festival
Date: Saturday, October 3, 2026
Location: Strugglebeard Bakery, 5221 S. Harper Court
Cost: FREE
Learn more about Cookies & Culture Festival here.
World Music Festival Chicago — Beverly Arts Center
Date: Saturday, October 3, 2026
Location: Beverly Arts Center, 2407 W. 111th St. Chicago, IL 60655
Learn more about World Music Festival Chicago here.
Barbara Bates 40th Anniversary Celebration
Date: Saturday, October 3, 2026
Location: Obama Presidential Center, 6001 S. Stony Island Ave. Chicago, IL 60637
Cost: Varies
Learn more about Barbara Bates 40th Anniversary Celebration here.
South Side Science Festival
Date: Saturday, October 3, 2026
Location: University of Chicago, Hyde Park
Cost: Free
Learn more about South Side Science Festival here.
The Hyde Park Kenwood Food Pantry
Date: Saturdays in October (October 3, 10, 17, 24, and 31, 2026)
Location: Hyde Park Union Church, 5600 S. Woodlawn Avenue
Cost: Free
Learn more about The Hyde Park Kenwood Food Pantry here.
Reuse-a-Palooza
Date: Sunday, October 4, 2026
Location: 1400 W 46th St, Chicago, IL 60609
Cost: FREE
Learn more about Reuse-a-Palooza here.
Bronzeville 5K Run/Walk
Date: Sunday, October 4, 2026
Location: 4433 S. St. Lawrence Ave., Chicago, IL 60653
Cost: $55 registration
Learn more about Bronzeville 5K Run/Walk here.
Seven Dollar Movie Night at the Harper Theater
Date: Tuesdays in October (October 6, 13, 20, and 27, 2026)
Location: Harper Theater, 5238 S. Harper Avenue
Cost: $7 tickets
Learn more about Seven Dollar Movie Night at the Harper Theater here.
Live Music at Daisy’s Po-Boy and Tavern – Charles Pryor
Date: Wednesdays in October (October 7, 14, 21, and 28, 2026)
Location: Daisy’s Po-Boy and Tavern, 5215 S. Harper Avenue
Cost: FREE
Learn more about Live Music at Daisy’s Po-Boy and Tavern – Charles Pryor here.
South Side Sweats Homecoming Game Day
Date: Saturday, October 10, 2026
Location: The Sport House, 1301 E. 47th St, Chicago, IL 60653
Cost: FREE
Learn more about South Side Sweats Homecoming Game Day here.
Southside Chicago Marathon Weekend
Date: Saturday, October 10, 2026
Location: Muffy’s Lounge & Components, 1322 E 67th St, Chicago, IL 60637
Cost: Varies
Learn more about Southside CHicago Marathon Weekend here.
Proof of Life: Stories from a Death Row Archive
Date: Saturday, October 10, 2026
Location: National Public Housing Museum, 919 S Ada St, Chicago IL
Cost: FREE
Learn more about Proof of Life: Stories from a Death Row Archive here.
Harvest Fest
Date: Saturday, October 10, 2026
Location: South Chicago Farm, 9001 S. Mackinaw Ave, Chicago, IL 60617
Cost: FREE
Learn more about Harvest Fest here.
53 Annual Historic Pullman House Tour
Date: Saturday, October 10 – Sunday, October 11, 2026
Location: Pullman Exhibit Hall, 1141 S Cottage Grove Ave, Chicago, IL 60628
Cost: $21
Learn more about 53 Annual Historic Pullman House Tour here.
14th Annual Chicago Day of the Girl
Date: Sunday, October 11, 2026
Location: Reva and David Logan Center for the Arts, 915 E 60th St Chicago, IL 60637
Cost: FREE
Learn more about Chicago Day of the Girl here.
Bears Vs. Packers Watch Party
Date: Sunday, October 11, 2026
Location: Ramova Theatre, 3520 S. Halsted Street, Chicago, IL 60609
Cost: FREE
Learn more about Bears Vs. Packers Watch Party here.
Karaoke Thursdays at Sip & Savor
Date: Thursday, October 15, 2026
Location: Sip & Savor, 78 E. 47th Street, Chicago IL, 60653
Cost: FREE
Learn more about Karaoke Thursdays at Sip & Savor here.
Afro Fashion Experience
Date: Saturday, October 17, 2026
Location: DuSable Black History Museum and Education Center, 740 E 56th Pl Chicago, IL 60637
Cost: Varies
Learn more about Afro Fashion Experience here.
Omar at Lyric Opera of Chicago
Date: Friday, October 23 – Wednesday, October 28, 2026
Location: Lyric Opera House, 20 N. Wacker Drive, Chicago IL , 60606
Cost: Varies
Learn more about Omar at Lyric Opera of Chicago here.
Black Girl Art Show
Date: October 25, 2026
Location: Zhou B Art Center, 1029 W 35th St, Chicago IL, 60609
Cost: Varies
Learn more about Black Girl Art Show here.
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