August has arrived, which means summer is starting to wind down. Whether you’re into outdoor festivals, cultural celebrations, family fun, or wellness experiences, August is filled with chances to soak up those final summer moments. We’ve rounded up a list of events to help you enjoy every last bit of the season. You’ll even find a few gems in other parts of the city to help you explore more of what Chicago has to offer.
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2025 Chicago Southsider Festival Guide
Lollapalooza Chicago 2025
Date: Thursday, July 31st – Sunday, August 3rd
Location: Grant Park in downtown Chicago, Illinois 60601
Cost: Varies
Learn more about Lollapalooza Chicago 2025 here.
The Black Women’s Expo 2025
Date: Friday, August 1st – Sunday, August 3rd
Location: McCormick Place, 2301 South Lake Shore Dr Chicago, IL 60616
Cost: Varies
Learn more about The Black Women’s Expo here.
Bronzeville Smooth Jazz Festival CarrCare Charity Pop-UP
Date: Saturday, August 2nd
Location: Mariano’s, 3857 South Doctor Martin Luther King Junior Drive Chicago, IL 60653
Cost: FREE
Learn more about Bronzeville Smooth Jazz Festival here.
Bud Billiken Parade
Date: Saturday, August 9th
Location: 35th & King Drive – Washington Park, Chicago IL 60653
Cost: FREE
Learn more about the Bud Billiken Parade here.
Artini – Where Art, Music and Cocktails meet at Gallery Guichard
Date: Saturday, August 14th
Location: 436 E 47th St, Chicago, IL 60653
Cost: FREE
Learn more about Artini Cocktails at Gallery Guichard here.
Chicago Air and Water Show
Date: Saturday & Sunday, August 16th – 17th (Practice is Friday, August 15th)
Location: North Avenue Beach
Cost: FREE
Learn more about the Chicago Air and Water Show here.
Blues in the Parks
Date: Thursday, August 21st
Location: Robert Taylor Park, 39 W 47th St, Chicago, IL 60609
Cost: FREE
Learn more about Blues in the Parks here.
Navy Pier Fireworks
Date: Saturdays, August 2th – August 9th – August 16th – August 23th – August 30th
Location: 600 E. Grand Avenue, Chicago IL, 60611
Cost: FREE
Learn more about Navy Pier Fireworks here.
Chicago Black Dance Legacy Project
Performance: Unbound: Shattered Frames, Endless Visions
Date: Saturday, August 23rd
Location: Harris Theater, 205 E. Randolph, Chicago, IL, 60601
Cost: Use code “SOUTHSIDER5” at checkout to save $5 on tickets
Learn more about the Chicago Black Dance Legacy Project here.
Bulls Fest
Date: Saturday, August 23rd – Sunday, August 24th
Location: United Center, 1901 W Madison St, Chicago, IL 60612
Cost: FREE
Learn more about the Bulls Fest here.
Milk & Melanin Festival 2025
Date: Saturday, August 23rd
Location: South Side Sanctuary, 4702 South King Drive, IL 60615
Cost: FREE
Learn more about the Milk & Melanin Festival here.
Chicago House Music Festival and Conference
Date: Saturday, August 23rd – Sunday, August 24th
Location: Millennium Park, Chicago, IL 60602 – Chicago Riverwalk Confluence, Franklin Street and Lake Street Chicago, IL 60601
Cost: FREE
Learn more about the Chicago House Music Festival and Conference here.
African Festival of the Arts Chicago
Date: Saturday, August 30th – Monday, September 1st
Location: Dusable Museum Sunken Garden, 5500 South Cottage Grove, Chicago, IL 60637
Cost: Varies
Learn more about the African Festival of the Arts here.
Chicago Jazz Festival
Date: Thursday, August 28th – Sunday, August 31st
Location: Millennium Park, Chicago, IL 60602
Cost: FREE
Learn more about the Chicago Jazz Festival here.
What festivals are you attending this summer? Did we miss a festival? Comment below and let us know!
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