THIS WEEKEND IN CHICAGO – Labor Day Weekend Ushers In Summer’s Final Days!
Make the most of your extended Labor Day Weekend with these top events that come with no shortage of ways to soak up the summer season’s final days while honoring the American worker!
A free event takes place in Millennium Park (55 N. Michigan Ave.) in the Loop with the Chicago Jazz Festival this Saturday and Sunday. This Labor Day weekend tradition promotes all forms of jazz featuring a lineup that runs the gamut from jazz legends to influential modern masters to crucial new voices to Chicago’s very own local talent along with national and international artists for over 40 years. Wrapping up Saturday evening’s performances at the Jay Pritzker Pavilion is Kermit Ruffins & the Barbeque Swingers with Eliades Ochoa closing out Sunday’s performances. You won’t be disappointed at Chicago’s oldest, free lakefront music festival!
Enjoy Chicago’s most mouth-watering event of the summer at WingOut Chicago 2025 this Saturday and Sunday (11:30 a.m.-8:30 p.m.) at Gallagher Way (3635 N. Clark St.) in the Wrigleyville neighborhood. Join in this all-out wing extravaganza with the city’s finest wing-slingers from Chicago’s best wing restaurants as they showcase their delicious creations that include classic buffalo, sweet-and-spicy, wood-smoked, Asian ginger, spicy garlic, honey chili, and a variety of other tantalizing flavors you won’t find anywhere else. Besides wing sampling this festival also features live music, adult beverages, competitions, and more. It’s the ultimate chicken wing block party not to be missed!
Another end of summer Labor Day weekend tradition takes place at the Copernicus Center (5216 W. Lawrence Ave.) in the Jefferson Park neighborhood with Taste of Polonia. This Polish heritage celebration features authentic Polish cuisine, a beer garden, non-stop live music, captivating dance performances, exhibitions, local vendors, a casino, movie screenings, carnival rides and games, and a dedicated Kids Stage offering a variety of exciting activities for the little ones. It’s a must-do family event that keeps both the little kids and adults happy!
This Saturday (10 p.m.) will be the final Navy Pier Fireworks for this summer season. The aerial display will originate from Navy Pier (600 E. Grand Ave.) in the Streeterville neighborhood with stunning views available from across the pier’s public spaces as well as from nearby beaches, while cruising along the Lakefront Trail, or from the pier’s various boat cruises. Come be awed by this grand finale!
Don’t miss this once-a-year event when bicycles reign on a car-free ride along Chicago’s DuSable Lake Shore Drive this Sunday (6:30 a.m.) for the annual Bike the Drive with the main location at Butler Field in Grant Park (235 S. Columbus Dr.) in the Loop. The 30-mile route runs down Lake Shore Drive from Bryn Mawr Avenue to 57th Street with various designated entry points along the way. The route will be dotted with rest stops, water and snacks as well. Cyclists can ride as little or as much of the 30-mile course then enjoy a post-ride festival in Grant Park. Plus, bike rentals are available for those without a bike. So there’s no excuse for you not to enjoy the sweeping views of the lake and skyline as you pedal your way down one of the city’s most scenic rides on its iconic lakefront roadway with no vehicle traffic!
Have a Happy, Safe and Enjoyable Labor Day Weekend Chicago!
