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Whether you’re ready or not, summer is coming to a close. It’s been a busy one, filled with monumental moments like the Obama Presidential Center opening, America’s 250th anniversary, WNBA All-Star Weekend, and so much more. But Labor Day weekend is here, and it’s finally time to say goodbye to summertime Chi.
With a sunny (for now) forecast predicted over the next few days, it’s only right to get out and make the most of the coveted three-day weekend and celebrate what the national holiday is all about: celebrating the contributions of the American worker.
Ready to send summer off with a bang? Here are our picks of the best events and things to do over the long weekend. For our full guide to more than 40 things to do this weekend, click here.
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1. Chicago Labor Day Parade & Eddie Fest
The Chicago Labor Day Parade returns to historic Pullman on Saturday. Organized by the Chicago Federation of Labor, the event celebrates union pride, solidarity and community togetherness. The parade will step off at East 112th Street and South Avenue F on the Southeast Side, before continuing north up South Ewing Avenue to East 106th Street. Afterwards, stick around for Eddie Fest, featuring live music, food and family-friendly activities, at Steelworkers Park.
2. Chicago Jazz Festival
As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows through Sunday at Pritzker Pavilion in Millennium Park and the Chicago Cultural Center during this annual festival. Visit the Chicago Jazz Festival website for the full lineup and schedule.
3. North Coast Music Festival
North Coast Music Festival brings some of the biggest names in EDM to Bridgeview, Illinois, from Friday through Sunday for beats and pyrotechnics in and around SeatGeek Stadium. The lineup includes big-name acts Fisher, Griz, Gryffin, Illenium and many more. And with multiple stages to explore, you should have no problem finding the house, techno, progressive and trance music that you want to dance to.
4. Bike the Drive
Take a car-free ride along DuSable Lake Shore Drive during this annual biking event on Sunday, which closes the lakeside thoroughfare to vehicle traffic and allows cyclists to ride through a 30-mile route dotted with rest stops, water and snacks. You'll have to wake up early (the course opens at 6:30am) and enter through one of the designated entry points along the road—but the novelty of biking on a stretch of pavement that is decidedly not bike-friendly is worth the hassle. Plus, proceeds from the event support the Active Transportation Alliance, a nonprofit organization working to improve conditions for pedestrians and cyclists throughout Chicago.
5. Snoop Dogg at Ravinia Festival
The oldest music festival in North America hosts more than 90 shows throughout the summer, featuring big-name headliners like Paul Simon, Alabama Shakes and Chance the Rapper. This weekend's highlights include Snoop Dogg's performance on Friday. Check out the full schedule of artists coming to Highland Park this year, and don't forget to pack a picnic.
6. Taste of Polonia
Feast on potato pancakes, kielbasa, pierogi, blitzes and more at this annual Polish celebration (the largest in the country) from Friday through Monday. Once you're full, stick around to take in performances from polka bands and tribute acts, play mini golf, shop from local vendors, watch traditional dance groups or try your luck in a casino.
7. Sound & Gravity
When Pitchfork Music Festival announced its sudden sunset at the start of 2025, Chicago’s music scene collectively wondered how festival co-founder Mike Reed would fill the sonic void. Turns out, Reed had an ace up his sleeve: Sound & Gravity, a four-day music marathon from Thursday to Sunday, featuring 50+ performances across seven venues in Bricktown and Avondale. Lineup highlights include Grouper, Alabaster DePlume, Son Lux and more. Read more about Sound & Gravity's inception here.
8. Hippo Campus at Gallagher Way
The Budweiser Concert Series is back at Gallagher Way, and Hippo Campus is taking the stage on Friday. GA and VIP tickets are available, and $1 from each ticket sold will go to the mental health and wellness organization Backline or the sustainability organization Reverb.
9. ARC Music Festival
The sixth annual ARC Music Festival is taking over Union Park from Friday through Monday, celebrating Chicago's house music roots and welcoming an international lineup of dance music artists. Expanding to a four-day sprawl for the first time, the fest features acts including Ben UFO, Honey Dijon, Carl Craig and Hiroko Yamamura. Catch sets at multiple stages spread throughout the park, enjoy food from local chefs, and don't skip the ARC After Dark parties at venues like Smartbar and Radius.
10. African Festival of the Arts
The annual festival, which celebrates art, music and food from across the African diaspora, returns from Saturday through Monday for its 36th edition. Head to Washington Park's Sunken Gardens for music and dance performances, vendors and cultural exhibits, and interactive workshops and family activities. Plus, indulge in African and Diasporan food and drinks.
11. The Great American Lobster Fest
Navy Pier is hosting this Labor Day weekend feast on Saturday and Sunday, featuring mountains of fresh seafood flown in from the East Coast. At the Great American Lobster Festival, hungry attendees can sign up for the Lobster Meal Experience, which includes one drink voucher and a full 1.25-pound lobster served with corn on the cob, potatoes, a dinner roll, fresh-cut lemons and melted butter. Once you're full, shop craft vendors and enjoy live music performances.
12. Live on the Lake
Friday through Monday are the last days to see free live music at the outdoor Navy Pier Beer Garden this year. The series features local, regional and national acts performing countless genres and musical styles every weekend. Check the Navy Pier website for the full lineup and schedule.
13. Chicago Architecture Center River Cruise aboard First Lady
Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Center River Cruise takes place aboard a First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline.