From hearing the blues to savoring cultural food festivals, there’s never a dull moment in Chicago. While some beloved South Side events like the Silver Room Block Party and the African Festival of the Arts have been canceled in recent years due to rising costs and other reasons, the city’s vibrant spirit lives on in many other celebrations.
Whether you’re visiting for the summer or call the city home, you’ll still find plenty of opportunities to dive into everything Chicago has to offer. If you want to join us for more events this year, subscribe to our newsletter and share this guide with a friend.
June 2025 Chicago Southsider Event Guide
Chicago Blues Festival
Date: Thursday, June 5th through Sunday, June 8th
Location:
Thursday: Ramova Theatre, 3520 S Halsted St., Chicago, IL 60609
Friday & Saturday: Millennium Park (Randolph & Monroe St Entrances)
Cost: FREE
Learn more about the Chicago Blues Festival here.
Contact the organizer here here or by phone at 312-744-5000.
Lincoln Park Greek Fest
Date: Friday, June 6th through Sunday, June 8th
Location: St. George Greek Orthodox Church, 2701 N Sheffield Ave, Chicago, IL 60614
Cost: FREE ($10 suggested donation)
Learn more about the Lincoln Park Greek Fest here.
Contact the organizer by email here or by phone at 773-525-1793.
57th Street Art Fair
Date: Saturday, June 7th & Sunday, June 8th
Location: Hyde Park, 57th St between Woodlawn & Kenwood Ave, Chicago, IL 60637
Cost: FREE
Learn more about the 57th Street Art Fair here.
Contact the organizer here or by phone at 773-729-1247.
44th Annual Puerto Rican Fest
Date: Thursday, June 12th through Sunday, June 15th
Location: Humboldt Park, 2800 W. Division St., Chicago, IL 60622
Cost: Varies
Learn more about the Puerto Rican Fest and purchase tickets here.
Contact the organizer by email here.
5th Annual Bronzeville Juneteenth Celebration
Date: Saturday, June 14th
Location: 35th and King Dr. Chicago, IL 60653
Cost: FREE
Learn more about the Bronzeville Juneteenth Celebration here.
Contact info the organizer by email here or by phone at (773) 285-9600.
Juneteenth Family Festival of Morgan Park
Date: Saturday, June 14th
Location: 110th and Longwood Chicago, IL 60643
Cost: FREE
Learn more about the Juneteenth Family Festival here.
Contact the organizer by email here.
11th Annual Juneteenth Parade
Date: Saturday, June 14th
Location: Madison St Sacramento Blvd to Central Park Ave, Chicago, IL 60624 – Post Parade Picnic in Garfield Park
Cost: FREE
Learn more about the Juneteenth Parade here.
Contact the organizer by email here.
9th Annual Juneteenth Black Bar Crawl – BEACH EDITION
Date: Saturday, June 14th
Location: Bellagio, 2229 S. Michigan Ave Chicago, IL 60616
Cost: Varies (21 and over)
Learn more about the Juneteenth Black Bar Crawl here.
Contact the organizer here or by phone at 773-426-1626.
Thai Festival Chicago
Date: Saturday, June 14th & Sunday, June 15th
Location: 851 W. Irving Park Rd Chicago, IL 60613
Cost: FREE
Learn more about the Thai Festival Chicago here.
Contact the organizer by email here.
Artini @ Gallery Guichard
Date: Thursday, June 12th
Location: Gallery Guichard – Bronzeville, 436 E 47th St Chicago, IL 60653
Cost: FREE
Learn more about Artini at Gallery Guichard here.
Contact the organizer here or by phone at 773-791-7003.
Annual Bronzeville Art District Trolley Tour 2025
Date: Wednesday, June 18th
Location: Gallery Guichard – Bronzeville, 436 E 47th St Chicago, IL 60653
Spaces: Blanc Gallery, Bronzeville Artists Lofts, Faie Afrikan Art, Gallery Guichard, Southside Community Arts Center
Cost: FREE
Learn more about the Bronzeville Art District Trolley Tour 2025 here.
Contact the organizer here or by phone at 773-791-7003.
Emancipation Ball
Date: Wednesday, June 18th
Location: Rockwell on the River, 3057 N Rockwell St. Chicago, IL 60618
Cost: Varies
Learn more about the Emancipation Ball here.
Contact the organizer by email here or by phone at (312) 961-3444.
Southside YMCA Juneteenth Celebration
Date: Saturday, June 21st
Location: 6330 S. Stony Island Ave, Chicago, IL 60637
Cost: FREE
Learn more about the Southside YMCA Juneteenth Celebration here.
Contact the organizer by phone at 312-932-1200.
Chicago Vegandale Festival 2025
Date: Saturday, June 21st & Sunday, June 22nd
Location: Grant Park, Butler Field – 100 S. Lake Shore Dr. Chicago, IL 60603 (between Monroe St and Jackson St)
Cost: Varies
Learn more about Chicago Vegandale Festival here.
Contact the organizer by email here.
Taste of Chicago Pop Up
Date: Saturday, June 28th
Location: Marquette Park, 6743 S. Kedzie Ave. Chicago, IL 60629
Cost: FREE
Learn more about the Taste of Chicago Pop Up here.
Contact the organizer here or by phone at 312-744-5000.
Millennium Art Festival
Date: Saturday, June 28th & Sunday, June 29th
Location: Lake Street at Michigan Chicago, IL 60601
Cost: FREE
Learn more about the Millennium Art Festival here.
Contact the organizer here or by phone at 847-926-4300.
4th Annual Ida B. Wells Festival
Date: Saturday, June 28th
Location: Ida B. Wells National Monument – 3729 S. Langley Chicago, IL 60653
Cost: VARIES
Learn more about the 4th Annual Ida B. Wells Festival here.
Contact the organizer by email: bturner@blackmetropolis.org
Chicago Pride Parade
Date: Sunday, June 29th
Location: 3900 N Broadway Chicago, IL 60613
Cost: FREE
Learn more about the Chicago Pride Parade here.
Contact organizer here or by phone at (312) 847-8093.
What festivals are you attending this summer? Did we miss a festival? Comment below and let us know!
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