Ah, three-day weekends! Whether you're traveling to the city from out of town or you're a local looking to take advantage of the last days of summer, we've got you covered. From massive music festivals to scenic bike rides, there is an endless array of Chicago Labor Day weekend events to enjoy. Check out this guide for the absolute best things to do in Chicago over Labor Day weekend.
Outdoor neighborhood festivals are a staple of Chicago summers. Labor Day weekend in Chicago is the perfect time to check one out while the weather is still ideal for being outside. From world-class art to international food fests, these are the top events in Chicago this Labor Day weekend.
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Get your culture on at the West Loop Art Fest. Take a stroll and enjoy over four blocks of amazing art, wine tastings, interactive experiences, children's crafts, and live music.
Plus, the West Loop plays an important role in the labor movement. Did you know we have 8-hour workdays because of the Haymarket Affair that took place right here? It’s a fitting spot to spend your Chicago Labor Day weekend. Today, it’s a foodie paradise.
See More: Join Chicago Food & City Tours after the art fest for a delicious inside look at this dynamic neighborhood via our Gateway To The West Loop Food Tour.
Source: African International House USA, Inc.
The African Festival of the Arts returns to Washington Park. Visitors will feel transported at this event that celebrates the cultures of the African Diaspora in a recreated African village. Listen to music, see movie screenings, and shop for African goods at one of the largest neighborhood festivals in the city.
Credit: Taste of Polonia Chicago
Taste of Polonia, America's largest Polish festival, happens in Chicago's Jefferson Park. Eat your fill of pierogis, kielbasa, and potato pancakes. Quench your thirst at the beer garden and get down to non-stop live music. Families can enjoy the Kids Stage, carnival rides, and even a casino for the adults!
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Wild about wings? Head to Gallagher Way in Wrigleyville for WingOut Chicago, a chicken wing extravaganza! Sample classic and creative flavors from over a dozen vendors while you listen to music right in front of the historic Wrigley Field.
For many, Labor Day weekend in Chicago is synonymous with massive music festivals. Whether you want free world-class jazz or high-energy dance beats, these festivals are the place to be.
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The Chicago Jazz Festival can be experienced at Millennium Park and the Chicago Cultural Center. Vibe out to music from legendary jazz icons and rising stars. Best of all? This iconic Chicago event is completely free to the public.
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If your idea of a relaxing three-day weekend involves waiting for the bass to drop, get tickets to North Coast Music Festival. Some of the biggest names in EDM converge at SeatGeek Stadium for several stages of house, techno, progressive, and trance music.
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Chicago is the birthplace of House Music, and ARC Music Festival is an all-out celebration of the genre. Head to Union Park to see some of the best dance music artists in the world put on epic shows across three days.
Think of Navy Pier as Chicago's playground on the lake. It is the perfect destination for Chicago Labor Day weekend activities and filled with many of the city's best restaurants and things to do.
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Navy Pier's spectacular Saturday fireworks reach their season finale over Labor Day weekend. This is your last chance of the year to watch the magic! Find a spot on the pier or book a fireworks dinner cruise for the best views.
While pop-up exhibits like Pixar Putt come and go, Flyover Chicago is the newest must-see immersive experience at Navy Pier. This multisensory flight attraction lets you "fly" over the city’s iconic skyline and landmarks, providing a thrilling perspective of Chicago.
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Brag to your friends that you dined at the largest rooftop deck in the country, Navy Pier's Offshore Rooftop. Enjoy delicious California-inspired cuisine and beautiful views of Lake Michigan. Whether you go for happy hour or a recovery Sunday brunch, Offshore Rooftop is a top-tier Chicago hotspot.
Take advantage of the late summer weather and get moving! From iconic bike rides to guided food walks, there is plenty to do to keep you grooving.
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For just one glorious morning, the famous DuSable Lake Shore Drive is closed to cars for a giant 30-mile bike ride. Grab your bike and join thousands of riders for Bike the Drive. It’s a once-a-year opportunity to see the skyline from the middle of the city's most famous road.
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Kickstart your Saturday with a free pilates or yoga class on the Great Lawn of Millennium Park. It’s the final class of the season, often accompanied by live music. Afterward, reward yourself with a stroll over to see "The Bean."
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See the city from the river on a kayak tour with Wateriders Chicago Kayak Tours and Rentals. Whether you choose a History & Architecture tour during the day or a Sunset Paddle at night, it’s one of the most unique ways to experience the city.
Feed your belly and your brain on a walking food tour! Chicago Food & City Tours is a TripAdvisor Travelers' Choice winner, which means you’re guaranteed a great time. Try our Iconic Foods of Chicago Tour for deep dish and Italian beef, or explore our Gateway to the West Loop Food Tour for a more modern culinary experience.
Film buffs have plenty of options that take you out of the dark theaters and into the fresh air.
Head to the FRIENDS™ Experience on Michigan Avenue. This immersive experience allows you to step inside the world of the iconic TV show. Sit on the orange couch, explore Monica’s kitchen, and take plenty of photos!
Source: Rooftop Cinema Club
With the Rooftop Cinema Club Fulton Market, you can watch a movie under the stars on the roof of the Emily Hotel. You’ll receive state-of-the-art headphones so you won’t miss a line of dialogue. Enjoy classic cinema snacks plus beer, wine, and cocktails while taking in the West Loop skyline.
Check out the vibrant themed pop-ups at The Highline or Lark. These spots frequently rotate immersive decor and themed menus that are perfect for a festive holiday weekend outing.
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ChiTown Movies brings a taste of the 1950s to Pilsen. Pile the whole family (including the dog) into the car for a classic drive-in experience. You can even order tacos and wings to be delivered right to your car window!
See More: Before the movie, book our Street Foods of Pilsen tour to try authentic foods in Chicago's coolest neighborhood!
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Whether you’re a Northsider or a Southsider, you can cheer on your favorite team. Both the Cubs and the Sox typically have home stands during Chicago Labor Day weekend, featuring giveaways, fireworks, and classic ballpark food.
Source; HBCU Gameday
The Chicago Football Classic returns to Soldier Field! This celebration of HBCUs (Historically Black Colleges & Universities) features a fierce football game, a Battle of the High School Bands, and a vendor marketplace.
We couldn't create a guide to Labor Day weekend in Chicago without including a celebration of the holiday itself. Check out below for more information about Chicago's Labor Day Parade.
Source: Chicago Tribune
Celebrate Labor Day weekend in Chicago in the historic Pullman District. This neighborhood has deep ties to the labor movement and is the perfect setting for the annual parade. Following the parade is Eddie Fest, featuring food and music honoring the great Chicago labor movement.
Interested in more Chicago events? Check out these guides!
17 Fun Things to Do in Downtown Chicago
Best Things to Do in Chinatown Chicago: 21 Restaurants & Attractions
25 Best Things to Do at Navy Pier & Top Places to Eat
Things To Do in Chicago for 4th of July: Your Ultimate Weekend Guide
