From plays to operas to cultural celebrations, there’s never a dull moment in Chicago. Whether you’re visiting for the spring or you call the city home, you’ll find plenty of opportunities to dive into everything Chicago has to offer.
We’ve curated a list of events that will help you experience the heart, soul, and flavor of the city. Plus, we’ve included a few happenings beyond the South Side to give you a broader taste of Chicago’s vibrant neighborhoods.
Get ready to experience the beat, the flavor, and the energy of Chicago like never before.
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May 2025 Chicago Southsider Event Guide
Scott Joplin’s Treemonisha – A Musical Reimagining
May 2nd – 4th, 2025
Location: Harris Theatre, Millennium Park, 205 E Randolph, Chicago, IL 60601
Cost: Varies
Purchase tickets to Treemonisha here.
Use discount code “SOUTHSIDER” for 25%, off by 11:59 pm on May 1st. Note: Not valid for premium seating. Limit 4 tickets per order. All sales are final.
Contact information here.
The Book of Grace
March 27th – May 18, 2025
Location: Steppenwolf Theatre Company, 1650 N. Halsted St, Chicago, IL 60614
Cost: Varies
Purchase tickets to The Book of Grace here
Contact information here.
Sounds of Progress: Opera and the Civil Rights Movement
May 10th, 2025, 2 pm
Location: DuSable Black History Museum and Education Center, 740 E. 56th Pl, Chicago, IL 60637
Cost: FREE
Learn more about Sounds of Progress here.
Contact information here
Policy: Running Numbers A Family Business. Gala & Awards Presentation
May 15th, 2025
Location: Harold Washington Cultural Center, 4701 South Doctor Martin Luther King Jr. Drive, Chicago, IL 60653
Learn more about Sounds of Policy.
Contact information here.
Chicago Food Truck Festival
May 16, 23, 30
Location: Daley Plaza, 50 W. Washington Street
Cost: FREE
Learn more about the Chicago Food Truck Festival here.
Contact information here.
Mole de Mayo Festival
Friday May 24th, 5 – 10 pm, Saturday, 25th, 12 – 10 pm, Sunday 26th, 12 – 9 pm, 2025
Location: 18th Street, between Morgan St and Halsted St, Chicago, IL
Cost: FREE
Learn more about the Mole de Mayo Festival here
Contact information here
Randolph Street Market
May 24 – 25th, 2025, 11 am – 3 pm
Location: 1341 W Randolph Street, Chicago, IL 60607
Cost: Varies
Learn more about the Randolph Street Market and get tickets here
Contact information here
Navy Pier’s Fireworks Show
May 24th, 2025- 9 pm
Location: Navy Pier, 600 E. Grand Blvd, Chicago, IL 60611
Cost: FREE
Learn more about the Navy Pier’s Fireworks Show here
Contact information here
Suenos Festival
May 25th – 26th, 2025, 12 – 10 pm
Location: Grant Park, Chicago, IL 60601
Cost: Varies
Learn more about the Suenos Festival and buy tickets here
Contact information here
C.R.D. Southside Chicago Memorial Day Parade
Monday, May 26th, 2025, 10 am – 1 pm
Location: 7750 S Emerald Ave, Chicago, IL 60620
Cost: FREE
Learn more about the C.R.D. Southside Chicago Memorial Day Parade here
Contact information here
Navy Pier’s Fireworks Show
May 28th, 2025, 9 pm
Location: Navy Pier, 600 E. Grand Blvd, Chicago, IL 60611
Cost: FREE
Learn more about the Navy Pier’s Fireworks Show here
Contact information here
Navy Pier’s Fireworks Show
May 31st, 2025, 10 pm
Location: Navy Pier, 600 E. Grand Blvd, Chicago, IL 60611
Cost: FREE
Learn more about the Navy Pier’s Fireworks Show here
Contact information here
What festivals are you attending this summer? Did we miss a festival? Comment below and let us know!
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