With long days and warm nights, summer weekends are made for exploring. Whether you’re staying local or venturing out, here are a few events worth adding to your calendar.
Kick Back at Jeff Fest
This longtime Jefferson Park tradition brings the neighborhood together for two days of music, food, and local flavor. Held in the heart of Jefferson Memorial Park, the festival features a mix of tribute bands, original acts, and a headline performance from Lucky Boys Confusion. In between sets, browse craft vendors, check out the kids’ zone, or just kick back with a cold drink and classic street fare.
Date: August 1-2
Time: Fri 5PM-10PM; Sat 1PM-10PM
Cost: $5 Fri; $10 Sat
Location: Jefferson Memorial Park, 4822 N Long Ave
More Info: bucketlisters.com
See Your Favorite Artists at Lollapalooza
Chicago’s biggest music festival returns to Grant Park with a stacked four-day lineup that spans pop, hip-hop, rock, EDM, and more. Headliners this year include Tyler, the Creator, Luke Combs, and Sabrina Carpenter… and that’s just a sample of the 170+ artists taking over multiple stages across the lakefront. Beyond the music, expect massive crowds, curated food and drink options, and plenty of festival fashion on display. Pro tip: hydrate early and plan your escape route.
Date: August 1-August 3
Time: 12PM-10PM
Cost: $189+
Location: Grant Park, 337 E Randolph St
More Info: lollapalooza.com
Soak Up the Sounds at 4th Annual Bronzeville Smooth Jazz Festival
Settle in for a soulful afternoon of live jazz at this community-focused festival in the heart of Bronzeville. Curated by local musician and producer Frank Goss III, the lineup includes standout sets from Phil Seed, Harlan Jefferson, and trumpet virtuoso Corey Wilkes. Bring a chair or blanket and snack on BBQ and soul food staples from Soul & Smoke while smooth grooves fill the air.
Date: August 2
Time: 12PM-8:30PM
Cost: Free
Location: Mariano’s Bronzeville, 3700 S Dr Martin Luther King Jr Dr
More Info: facebook.com
Feel the Energy at Fiesta del Sol
This decades-strong festival in Pilsen is one of the largest Latino celebrations in the Midwest, bringing together live music, art, food, and community pride. This event features everything from traditional folklórico dancing to carnival rides and engagement booths. Street vendors serve up tacos, elotes, and other Mexican fare, while the live stage hosts Latin pop, cumbia, and regional acts. It’s family-friendly, free to attend, and full of energy.
Date: August 1-3
Time: Fri 11AM-10PM; Sat 11AM-10PM; Sun 11AM-10PM
Cost: Free
Location: Cermak Rd from Ashland Ave to Morgan Ave
More Info: fiestadelsol.org
Step Into the 70’s at Mahogany in the Park
Part film screening, part ’70s-style block party, this outdoor event transforms Washington Park into a nostalgic celebration of Black cinema and culture. Dress in retro glam (think: platform shoes and dramatic collars) and settle in for a screening of Mahogany, presented by the Black Film Club and The DuSable Museum. Expect DJ sets, themed photo ops, and food from local vendors all part of the Park District’s Night Out in the Parks series.
Date: August 2
Time: 6PM-10PM
Cost: Free
Location: Washington Park, 5531 S King Dr
More Info: blkfilmclub.com
