Labor Day weekend in Chicago is more than just the unofficial end of summer - it’s one of the city’s busiest weekends for festivals, concerts, and neighborhood events. Whether you’re looking for live music, cultural celebrations, or just a good excuse to get outside, there’s no shortage of things to do. Here’s a rundown of some of the top events happening around town.
Chicago Jazz Festival | Aug 28–31 | Millennium Park
*Free admission
Free, world-class live jazz in the heart of the Loop. Bring a blanket and a low chair, grab coffee, and let the music do the rest. And afterwards, don’t skip a walk through the Riverwalk just a few blocks away.
ARC Music Festival | Aug 29–31 | Union Park
Chicago's premier house and techno fest - 3 days, 18+, with big names like Jamie xx, John Summit, Amelie Lens, FISHER, Honey Dijon, and Eric Prydz performing under his Pryda, Cirez D, and own-name monikers. The festival runs from 2–10 p.m. daily, plus nighttime “After Dark” club shows around the city. Take advantage of the night and stop in for dinner in the West Loop after the last set.
North Coast Music Festival | Aug 29–31 | SeatGeek Stadium, Bridgeview
If you’re after mass-scale EDM with immersive art and DJ sets, this is the spot to hit. Just outside the city, but always worth it for the headliners.
Taste of Polonia | Aug 29–Sept 1 | Jefferson Park
One of the city’s biggest cultural festivals and the largest Polish festival in the USA. This annual Labor Day weekend taste fest in Chicago offers non-stop live music, food, entertainment, and fun for four days. It’s a must-do family event with enough scheduling to keep both little kids and adults happy. Authentic Polish eats, live music, local artisans, family-friendly and full of flavor.
Bike the Drive | Sunday, Aug 31 | Lake Shore Drive
Car-free, bike-friendly. A rare morning on Lake Shore Drive when you can just ride without cars. Stunning skyline, no horns. Start south at 5:30 a.m. for the clearest ride and best sunrise views.
Chicago Labor Day Parade & Eddie Fest | Saturday, Sep 6 | Pullman
Historic roots, real neighborhood energy. March, then stick around for food trucks, live music, and a real sense of community. Find more information here.
Cubs vs. Braves | Sept 1 | Wrigley Field
Classic end-of-summer energy. Day game, rivalry matchup, and Wrigley as it should be experienced. Get your tickets here.
Other Notables
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WingOut Chicago – Wings, music, and Gallagher Way energy.
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Candlelight Concerts – Intimate tribute shows that cover Coldplay, Fleetwood Mac - by candlelight.
Labor Day is also a reminder that fall market is right around the corner.
If you’ve been enjoying summer but also thinking about making a move, now’s the time to get serious before the holidays sneak up. The fall market moves fast, and buyers and sellers who act early get the best results.
Enjoy the last of summer’s big events, and when you’re ready to talk about your next step in Chicago real estate, I’d love to help. Call or text me at (773) 865-5661 or email [email protected]
