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.
Swing Into the Chicago Jazz Festival
Head to Millennium Park over Labor Day weekend for the Chicago Jazz Festival, featuring jazz legends like Monty Alexander, Kermit Ruffins & the Barbeque Swingers, and Eliades Ochoa. Expect world-class performances across multiple stages celebrating the rich history of jazz in the city. Free and open to all, this festival is a can’t-miss for music lovers.
Date: August 28-31
Time: Thu 11AM-7:30PM; Fri 11:30AM-9PM; Sat & Sun 11AM-9PM
Cost: Free
Location: Various Locations
More Info: chicago.gov
Get a Taste of Polonia
Celebrate Polish culture at the Taste of Polonia Festival, the largest Polish festival in the U.S. This four-day Labor Day weekend event features live music, traditional dance, authentic cuisine and beer, over 30 local vendors, and a Kids Zone packed with activities.
Date: August 29-September 1
Time: Fri 5PM-10:30PM; Sat & Sun 12PM-10:30PM; Mon 12PM-9:30PM
Cost: $10+
Location: Copernicus Center, 5216 W. Lawrence Ave.
More Info: topchicago.org
Take a Bite of WingOut Chicago 2025
Chicago’s wing lovers unite for this weekend-long festival of bold flavors, live music, and cold drinks. Sample wings from top local restaurants like Jake Melnick’s Corner Tap, Smoke Daddy, and Rizzo’s Bar & Inn, plus dozens more. From spicy to sweet, traditional to exotic, it’s a wing extravaganza you won’t want to miss.
Date: August 30-31
Time: 11:30AM-7:30PM
Cost: $25+
Location: Gallagher Way, 3635 N. Clark St.
More Info: wingout.greencurtainevents.com
Dance All Night at ARC Music Festival
Get ready for three days of high-energy performances at ARC Music Festival. Headliners include John Summit, SJ Sneak, and Malugi, bringing house, electronic, and dance beats to Chicago’s festival scene. Fans can expect immersive light shows, curated stages, and a weekend filled with nonstop music, food, and good times.
Date: August 29-31
Time: 2PM-10PM
Cost: $189+
Location: Union Park, 1501 W. Randolph St.
More Info: arcmusicfestival.com
Cruise the City at Bike the Drive
Take over Lake Shore Drive on two wheels during this once-a-year Chicago tradition. Ride as little or as much of the 30-mile course as you like while enjoying sweeping views of the lake and skyline. After the ride, enjoy a post-ride festival in Grant Park with music, food, and family-friendly activities. Bike the Drive welcomes cyclists of all ages and abilities, making it a perfect way to get active and enjoy the city from a new perspective.
Date: August 31
Time: 6:30AM
Cost: $68+
Location: Butler Field, 235 S. Columbus Dr.
More Info: bikethedrive.org
