Home Things To Do Chicago Southsider Summer Festival and Event Guide – August 2024

Chicago Southsider Summer Festival and Event Guide – August 2024

Explore Chicago's summer festivals and events celebrating food, history, music, and culture.

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August is here, which means that summer is winding down. But you still have a few weeks to soak up the sun and participate in community events across Chicago’s South Side.

From outdoor festivals and cultural celebrations to family-friendly activities and wellness workshops, this month is packed with opportunities to make the most of the remaining summer weeks. We’ve put together a list of events that will help you savor the city this summer. You’ll also find a few events in other parts of the city to give you a chance to explore all that Chicago has to offer.

Chicago Southsider would like to thank our contributor, Sunny Rock, for compiling the events for August 2024. If you appreciate our work or want to support the mission of Chicago Southsider, please subscribe to our weekly newsletter and share this article with your network.

Mark your calendars for these upcoming events in August!

2024 Chicago Southsider Festival Guide

Lollapalooza Chicago 2024

Thursday-Sunday August 1st, 2nd, 3rd & 4th 2024

Location: Grant Park in downtown Chicago, Illinois

Cost: Varies

Learn more about Lollapalooza Chicago 2024 here


Chicago Belize Day in the Park

Sunday, August 4th, 2024, 12:30- 10:30 pm

Location: Burnham Park in Bronzeville Chicago

Cost: FREE

Learn more about Chicago Belize Day in the Park here


Pianos in the Park 

Thursdays, August 1st, 8th & 15th 2024, 1 – 2 pm & 2:30 – 3:30 pm

Location: Bessemer Park – 8930 S Muskegon & Jackson Park – 6401 S Stoney Island, Chicago, IL

Cost: FREE

Learn more about Jazzin on the Steps here


Blues in the Parks – Nick Alexander

Friday, August 9th 2024, 6 – 8 pm

Location: Burnside Park, 9400 S. Greenwood Ave. Chicago, IL

Cost: FREE 

Learn more about the Blues in the Parks here


Bud Billiken Parade

Saturday, August 10th 2024, 10 am – 4 pm

Cost: FREE

Learn more about the Bud Billiken Parade here


Chicago Air and Water Show

Saturday & Sunday, August 10th – 11th, 2024, 10:30 am – 3 pm – (Practice is Friday, August 9th)

Location: North Avenue Beach

Cost: FREE

Learn more about the Chicago Air and Water Show here


Northalsted Market Days 

Saturday & Sunday, August 10th – 11th 2024

Location: Halsted St: from Belmont to Addison Chicago, IL

Cost: FREE (suggested donation of $20)

Learn more here


The Brown Derby Jazz Series – 2nd Mondays of March – December 

Monday, August 12, 2024, 6 – 8 pm

Location: St. Moses the Black Parish Ministry Center, 7749 South Vernon Chicago, IL

Cost: FREE

Learn more about Jazzin on the Steps here


Jazzin on the Steps – 2nd Tuesday Jazz Jam

Saturday, August 13th 2024, 7 – 10 pm

Location: St. Moses the Black Parish Ministry Center, 7749 South Vernon Chicago, IL

Performer: Nanette Frank

Cost: FREE

Learn more about Jazzin on the Steps here


Deeply Rooted Dance Theater – Deeply at Dusk: Deeply Does the Classics

Thursday, August 15th 2024, – 7:30 – 8:30 pm

Location: South Shore Cultural Center/Field House – 7059 S. Shore Dr. Chicago, IL 60649 

Cost: FREE

Learn more about Deeply Rooted Dance Theater here


18th Annual Bronzeville Art District Trolley Tour 2024

Friday, August 16th 2024, 6 – 9pm (3rd Fridays throughout summer)

Location: Gallery Guichard, 436 E. 47th St. Chicago, IL 60653

Cost: FREE

Learn more about the Bronzeville Art District Trolley Tour here


Blues in the Parks – Joey Saye Trio w/Bob Stroger & Kennedy “Beadey Eyes” Smith

Friday, August 16th 2024, 6 – 8 pm

Location: Tilton Park, 230 N Kolmar Ave. Chicago, IL

Cost: FREE 

Learn more about the Blues in the Parks here


Taste of Chicago: Pullman Park

(Grant Park Main Festival Moved from July to Sept 6-8th, due to NASCAR and packed Grant Park schedule)

Saturday, August 17th 2024, 12 – 8 pm

Location: Pullman Park, 11101 S. Cottage Grove Ave. Chicago, IL

Cost: FREE

Learn more about the Taste of Chicago here


South Chicago Dance Theatre Season 7: Dance for Life

Monday, August 19th 2024 – 6 pm

Location: Auditorium Theatre

Cost: Varies

Learn more here


Deeply Rooted Dance Theater – Divination: The Dancing Souls of Black Folk

Saturday, August 24th 2024, 5:45 – 7:00 pm

Location: Millenium Park / Jay Pritzker Pavilion – 201 E. Randolph St. Chicago, IL 60601

Cost: FREE

Learn more about Deeply Rooted Dance Theater here


Jazzin on the Steps – 4th Sundays

Saturday, August 25th 2024, 4 – 6:30 pm

Location: St. Moses the Black Parish, 331 East 71st St 

Performer: Tim Fitzgerald

Cost: FREE

Learn more about Jazzin on the Steps here


Chicago Jazz Festival

Thursday – Sunday, August 29th – Sept 1st 2024

Location: Millenial Park

(Entrances = Michigan Ave/Washington St., Michigan Ave/Madison St., Randolph St. & Monroe St)

Cost: FREE

Learn more here

What festivals are you attending this summer? Did we miss a festival? Comment below and let us know!


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