September is stacked with reasons to get out and explore Chicago’s South Side. We’ve curated a list of events taking place this month to help you make the most of it.
If you like this guide, subscribe to Chicago Southsider on Substack and pass it along to a friend.
South Side Events for September 2026
Seven Dollar Movie Night at the Harper Theater
Date: Tuesdays in September (September 1, 8, 15, 22, and 29)
Location: Harper Theater, 5238 S. Harper Avenue, Chicago, IL 60615
Cost: $7 tickets; small sodas, popcorn, and hot dogs are $4 each
Learn more about Seven Dollar Movie Night at the Harper Theater here.
Components Running Crew
Date: Tuesdays in September (September 2, 9, 16, 23, and 30)
Location: Components, 1322 E. 67th Street, Chicago, IL 60637
Learn more about Components Running Crew here.
Live Music at Daisy’s Po-Boy and Tavern – Charles Pryor
Date: Tuesdays in September (September 2, 9, 16, 23, and 30)
Location: Daisy’s Po-Boy and Tavern, 5215 S. Harper Avenue, Chicago, IL 60615
Learn more about Live Music at Daisy’s Po-Boy and Tavern – Charles Pryor here.
Chicago Jazz Festival
Date: Thursday, September 3 – Sunday, September 6, 2026
Location: Millennium Park, 201 E. Randolph St., Chicago, IL 60601
Cost: Free
Learn more about Chicago Jazz Festival here.
Cookies and Karaoke at Strugglebeard Bakery
Date: Fridays in September (September 4, 11, 18, and 25)
Location: Strugglebeard Bakery, 5221 S. Harper Court, Chicago, IL 60615
Learn more about Cookies and Karaoke at Strugglebeard Bakery here.
The Hyde Park Kenwood Food Pantry
Date: Saturdays in September (September 5, 12, 19, and 26)
Location: Hyde Park Union Church, 5600 S. Woodlawn Avenue, Chicago, IL 60637
Learn more about The Hyde Park Kenwood Food Pantry here.
Pullman Labor Day Parade
Date: Saturday, September 5, 2026
Location: Chicago’s 10th Ward, Pullman, Chicago, IL 60628
Cost: Free
Learn more about Pullman Labor Day Parade here.
African Festival of the Arts
Date: Saturday, September 5 – Monday, September 7, 2026
Location: Washington Park, 5531 S. Martin Luther King Jr. Dr., Chicago, IL 60637
Cost: Varies
Learn more about African Festival of the Arts here.
Hyde Park Farmers Market
Date: Saturdays in September (September 6, 13, 20, and 27)
Location: Hyde Park Bank Parking Lot, 1525 E. 53rd St., Chicago, IL 60615
Learn more about Hyde Park Farmers Market here.
First Sunday Walking Tour
Date: Sunday, September 6, 2026
Location: Historic Pullman Foundation Exhibit Hall, 11141 S. Cottage Grove Ave., Chicago, IL 60628
Cost: $15
Learn more about First Sunday Walking Tour here.
Learn to Knit Series
Date: Sundays in September (September 7, 14, 21, and 28)
Location: Fiber Friends Studio, 1744 E. 55th Street, Chicago, IL 60615
Cost: $145
Learn more about Learn to Knit Series here.
Harper Court Summer Music Series
Date: Thursday, September 10, 2026
Location: Harper Court, 5253 S. Harper Court, Chicago, IL 60615
Learn more about Harper Court Summer Music Series here.
Jazz in the Court
Date: Friday, September 11, 2026
Location: 5235 S. Harper Court
Learn more about Jazz in the Court.
Camp Lonestar
Date: Friday, September 11, 2026
Location: 2100 S. Morgan Street
Learn more about Camp Lonestar.
79th Street Renaissance Festival
Date: Saturday, September 12, 2026
Location: 79th Street and Racine Avenue
Cost: Free
Learn more about 79th Street Renaissance Festival here.
Generation Wealth Conference
Date: Saturday, September 12, 2026
Location: Obama Presidential Center, 6001 S. Stony Island Ave.
Cost: Varies
Learn more about Generation Wealth Conference here.
Chicago Football Classic
Date: Sunday, September 12, 2026
Location: Soldier Field, 1410 S. Museum Campus Drive, Chicago, IL 60605
Cost: Varies
Learn more about the Chicago Football Classic here.
Printers Row Lit Fest
Date: Saturday, September 12 – Sunday, September 13, 2026
Location: South Dearborn Street between Ida B. Wells Drive and Polk Street, Chicago, IL 60605
Cost: Free
Learn more about Printers Row Lit Fest here.
Englewood Music Fest
Date: Saturday, September 12, 2026
Location: 6401 S. Halsted Street
Cost: Ticketed
Learn more about Englewood Music Fest here.
Guida Family Creative Wing Open Studio Night
Date: Thursday, September 17, 2026
Location: Hyde Park Art Center, 5020 S. Cornell Avenue, Chicago, IL 60615
Learn more about Guida Family Creative Wing Open Studio Night here.
Topdog/Underdog at Steppenwolf Theatre
Date: Thursday, September 17 – Sunday, November 1, 2026
Location: Steppenwolf Theatre, 1650 N. Halsted St. 60614
Learn more about Topdog/Underdog here.
Chicago Bears Paint n’ Sip!
Date: Friday, September 18, 2026
Location: 8509 S. Ashland Ave., Chicago, IL 60620
Cost: $30 Materials Fee (All supplies included), BYOW – Bring Your Own Wine & a Light Snack
Learn more about Chicago Bears Paint n’ Sip! here.
Raices Latine Heritage Month Art Gallery Opening Reception
Date: Friday, September 18, 2026
Location: Vjosa Cafe & Events, 1010 W 35th St Ste 102, Chicago, IL 60609
Cost: Free
Learn more about Raices Latine Heritage Month Art Gallery Opening Reception here.
Hispanic Heritage Month Block Party
Date: Saturday, September 19
Location: Back of the Yards Coffee, 1621 W 47th St, Chicago, IL 60609
Cost: Join the waitlist
Learn more about Hispanic Heritage Month Block Party here.
Chicago Live!
Date: Saturday, September 19 – Sunday, September 20, 2026
Location: Navy Pier, 600 E. Grand Ave., Chicago, IL 60611
Cost: Free
Learn more about Chicago Live! here.
Ecologies of Architecture: Aleksandra Kędziorek and Jeff Carter in Conversation
Date: Saturday, September 19, 2026
Location: Hyde Park Art Center, 5020 S. Cornell Avenue, Chicago, IL 60615
Learn more about Ecologies of Architecture: Aleksandra Kędziorek and Jeff Carter in Conversation here.
Nile Noir: A Belly Dance Cabaret
Date: Saturday, September 19, 2026
Location: Connect Gallery, 1451 E. 53rd Street, Chicago, IL 60615
Cost: $40
Learn more about Nile Noir: A Belly Dance Cabaret here.
Pullman Labor History Tour
Date: Saturday, September 20, 2026
Location: Historic Pullman Foundation Exhibit Hall, 11141 S. Cottage Grove Ave., Chicago, IL 60628
Cost: $20
Learn more about Pullman Labor History Tour here.
FASTLANE House Music Dance Party
Date: Friday, September 25
Location: Visions Odeum and Events, 11901 South Loomis Street, Chicago, IL 60643
Cost: $30 Pay at the Door
Learn more about FASTLANE House Music Dance Party here.
African/Caribbean International Festival of Life
Date: Friday, September 25 – Sunday, September 27, 2026
Location: Union Park, 1500 W. Randolph Street, Chicago West Loop
Cost: Varies
Learn more about African/Caribbean International Festival of Life here.
World Music Festival Chicago
Date: Friday, September 25 – Sunday, October 4, 2026
Location: Multiple locations throughout Chicago
Cost: FREE
Learn more about World Music Festival Chicago.
Bronzeville Summer Nights
Date: Saturday, September 26, 2026
Location: East 47th St. (Wabash – Cottage Grove)
Learn more about Bronzeville Summer Nights.
Tacos & Tequila Festival
Date: Saturday, September 26, 2026
Location: Northwestern Medicine Field
Learn more about Tacos & Tequila Festival.
Tsukimi Moon Viewing Festival
Date: Saturday, September 26, 2026
Location: Chicago Park District Osaka Garden, Jackson (Andrew) Park, 6401 S. Stony Island Ave. Chicago, IL 60637
Learn more about Tsukimi Moon Viewing Festival here.
Beverly Art Walk
Date: Saturday, September 26, 2026
Location: Beverly/Morgan Park, Chicago, IL 60643
Learn more about Beverly Art Walk.
Hyde Park Jazz Festival
Date: Saturday, September 26 – Sunday, September 27, 2026
Location: Reva and David Logan Center for the Arts, 915 E. 60th St., Chicago, IL 60637, plus neighborhood stages
Cost: Free
Learn more about Hyde Park Jazz Festival here.
Q&A with Artist Kari Blak
Date: Saturday, September 26, 2026
Location: Hyde Park Art Center, 5020 S. Cornell Avenue, Chicago, IL 60615
Learn more about Q&A with Artist Kari Blak here.
Pullman Exhibit Hall Open
Date: Throughout September
Location: Historic Pullman Foundation Exhibit Hall, 11141 S. Cottage Grove Ave., Chicago, IL 60628
Learn more about Pullman Exhibit Hall Open here.
Support local entrepreneurs and community news by subscribing to the Chicago Southsider! Thank you for your support.
