Labor Day traditionally denotes the end of the summer season and, since 1882, represents an annual workers’ holiday on the first Monday of September. And Chicago knows how to celebrate this three-day event in fine fashion!
While most residents prefer barbecues and weekend cruise parties outside New York. Explore the best activities & things to do in Chicago during Labor day weekend.
1) Check out a music festival
You can’t do Labor Day in Chicago without checking out one of the city’s annual music festivals. This year, the weekend is packed with a diverse line-up of fests — catch a free concert under the stars in Millennium Park, experience authentic Latinx music and culture in Pilsen, dance the night away at a new house music festival, and more.
ARC Music Festival:- This new fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.
Chicago in Tune:- This new music festival will feature free and ticketed events at venues around the city and iconic Millennium Park.
North Coast Music Festival: This annual Labor Day weekend music festival includes electronic music, hip hop, and rock acts, plus art installations and food vendors.
2) Fill up at a food fest
Get a taste of our diverse dining scene at these Labor Day weekend food events. Dig into the best local burgers, fill up on tacos from a street vendor, and indulge in traditional Polish fare.
Roscoe Village Burger Fest: Find the best burger in the city at this local favorite, all while enjoying live music and cold drinks.
Maxwell Street Market: This Sunday market is a Chicago tradition with an eclectic mix of handmade crafts, live music, family fun, and some of the best street food in Chicago.
3) Take a boat cruise
Set sail on one of Chicago’s famous boat cruises. Choose from informative architecture tours, fast-paced speedboat rides, unforgettable dinner cruises, Here’s just a few boat cruises happening on the water this Labor Day weekend:
Labor Day Weekend Afternoon Booze Cruise on Saturday, September 4th, Anita Dee - Celebrate Labor Day On the Water! Enjoy Amazing Skyline Views, a Full Bar with Cocktails Available For Purchase, & Music.
4) Explore the Chicago Riverwalk
Where else can you find an urban canyon filled with delicious food, cocktails, public art, and stunning views? The Chicago Riverwalk is open to enjoy all Labor Day weekend long. It’s the perfect spot to hop on a boat tour, admire the surrounding architecture, and enjoy a drink with waterfront views.
5) Catch a baseball game
The regular season might be winding down, but you still have time to catch the Chicago Cubs play at historic Wrigley Field. One of the oldest MLB stadiums in the country, seeing a game at Wrigley is truly a bucket list experience.
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