While there's no shortage of ways to celebrate Labor Day, the holiday weekend often lands as bittersweet, marking the unofficial end of summertime and all the sun-soaked bliss that comes with it. Thankfully, there’s still plenty of warm weather fun to be had as we roll into the three-day weekend, from street festivals (like West Loop Art Fest) to live music at the Chicago Jazz Festival downtown and North Coast in suburban Bridgeview. It’s also the final weekend to catch free fireworks shows at Navy Pier. Scroll through for even more stuff to do and have a very happy Labor Day.
RECOMMENDED: Your guide to Labor Day weekend 2025 in Chicago
We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring 18 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.
During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays and Saturdays) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.
Take a car-free ride along DuSable Lake Shore Drive during this annual biking event, which closes down 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 from one of designated entry points along the road—but the novelty of biking on a stretch of pavement that is decidedly not bike-friendly is well worth the hassle. Plus, proceeds from the event support the Active Transportation Alliance, a nonprofit organization that working to improve conditions for pedestrians and cyclists throughout Chicago.
As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows at Pritzker Pavilion in Millennium Park and the Chicago Cultural Center during this annual festival. Headliners include composer Esperanza Spalding, saxohponist Ari Brown and drummer Greg Fundis. Visit the Chicago Jazz Festival webpage for the full lineup and schedule.
The fifth annual ARC Music Festival is scheduled to take over Union Park during Labor Day weekend, celebrating Chicago's house music roots and welcoming an international lineup of dance music artists. Taking place across three days, the fest features acts like Richie Hawtin, Arielle Free, Felix Da Housecat, Jamie xx and Octo Octa. 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.
For some, Labor Day weekend means cookouts and enjoying some of the final days of summer among family and friends. For other, it means crowding in front of a stage with a bunch of strangers and dancing to the sound of bone-rattling bass drops. North Coast Music Festival brings some of the biggest names in EDM to Bridgeview, Illinois, for three days of beats and pyrotechnics in and around SeatGeek Stadium. With multiple stages to explore, you should have no problem finding the house, techno, progressive and trance music that you want to dance to.
After a one-year hiatus, the African Festival of the Arts—which celebrates art, music and food from across the African diaspora—returns this Labor Day weekend. Head to Washington Park to wander around a recreated African village complete with vendors, stilt walkers, African fine art and fabrics, a quilt pavilion, drum circles and more interactive features; plus, catch live music from various acts. When you get hungry, swing by the Bank of the Nile food court, which features food from cultures across Africa and beyond.
Feast on potato pancakes, kielbasa, pierogi, blitzes and more at this annual Polish celebration (the largest in the country) during Labor Day weekend. Once you're full, stick around to take in performances from polka bands and tribute acts, grab drinks in a beer garden, shop from local vendors, watch traditional dance groups or try your luck in a casino.
While this parade doesn't take place on Labor Day weekend itself, it's still a can't-miss event. The Chicago Labor Day Parade returns to historic Pullman on September 6. Organized by the Chicago Federation of Labor, the event celebrates union pride, solidarity and community togetherness. The parade will step off at 107th Street and head south down Cottage Grove Avenue to 112th Street. Afterwards, stick around for Eddie Fest, featuring live music, food and family-friendly activities.
During the summer, spending more time indoors than absolutely necessary feels almost sacrilegious. The Music Box Theatre gets it—and fully embraces the season by inviting movie lovers into its charming outdoor garden. Grab a specialty cocktail (each one cleverly named after an iconic film) and settle in for a night of cinema under the stars. Adventure comedy classic The Goonies will be screened Monday, September 1, through Thursday, September 4.
What's making Chicago summers even cooler? The Sugar Hole, an ice cream hut sharing a building with multidisciplinary arts venue Color Club that's staffed entirely by...puppets? When The Sugar Hole opens up shop, a rotating cast of puppets pops through a black porthole to take customers' orders and cause general mayhem.
While the Bears enjoy their last few weeks of the offseason, Soldier Field will be hosting some of the biggest names in music for the holiday weekend. Oasis will kick things off on Thursday, August 28, for one of the most hotly anticipated reunions of the decade. The day after, My Chemical Romance will celebrate the 19-year anniversary of The Black Parade with new wave legends Devo opening. Indie folk outfit The Lumineers rounds off the weekend of steady gigs.
Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.
Have you ever watched the DJ at one of Chicago's many dance parties with envy and thought, “I wanna do that”? Now you can, thanks to Boehlen Curation's inclusive DJing 101 class. The class—catering to women and members of the LGBTQ community—will teach the fundamentals of DJing, offer practice time on real decks and provide guidance and feedback from Chicago pros. The workshop promises to be intimate, with a maximum of 21 guests, so the environment is sure to be welcoming and informative.
Spin classes and weight lifting can wait for the winter. This summer, jump start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn every Saturday from May through August.
The oldest music festival in North America plays host to more than 100 shows throughout summer, featuring big-name headliners like Janelle Monáe, Lenny Kravitz and James Taylor. Check out the full schedule of artists coming to Highland Park this year. Don't forget to pack a picnic!
What do true crime and deep sea diving have in common? Enough to fill a whole book, according to local author Matthew Gavin Franks. Celebrate the release of Submersed: Wonder, Obsession, and Murder, in the World of Amateur Submarines with a coterie of local writers. The event will include readings from the Random House release and a conversation between Matthew and writer Tori Rego. Books will be provided by Madison Street Books.
Rooftop Cinema Club, the open-air theater perched atop The Emily Hotel, is back for another season. Guests can catch showings of hand-picked classics, cult films and recent releases while also enjoying sweeping views of the skyline and craft beverages. It’s the perfect summer cinema experience. Check the official website for the full schedule and lineup.
Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full schedule.
Chicago DJs take over the Wave Wall at Navy Pier every Saturday through August to play free, live sets of house and dance music. The outdoor series features names like Steve Miggedy Maestro, Zeetus Lapetus, Gabriel “Rican” Rodriguez, Oliver Fade, Ron Carroll and more.
Channel the artist within using cakes and cookies as your palette with a workshop at Bon Vivant! After feasting on snacks and cocktails, a team of experienced bakers offers tips, tricks and techniques for creating your own creative confections. Workshop themes for Labor Day weekend include “Chicago Cookout” and “Fancy Picnic.” View the full workshop lineup here.
With its latest exhibition, the Chicago Botanic Garden showcases the patterns and prints that adorn the natural world. Through meticulously planted gardens and nature-inspired art installations, Patterned by Nature highlights the intersection between graphic design and horticulture. Exhibition highlights include colossal embroidered flowers by Raquel Rodrigo, a collection of upcycled fashion sourced from garden materials by Columbia College Chicago’s School of Fashion and a paisley patterned succulent garden.
A spot on the pine bleachers at Drip Collective has become one of the most coveted seats in the city, thanks to the cafe's adventurous beverage menu (hello, mango sticky rice matcha latte!) and hyper-local event programming. Aside from piping hot coffee, Drip has been bringing a different kind of heat this summer with Hot Drip Sessions, a weekends-only DJ pop-up. August marks Hot Drip Sessions' last installment of the summer, featuring house, cumbia and afrobeat sets from locals like Aced Spade, ADONIA and more.
Can't make it to West Loop? Drip Collective has been uploading past Hot Drip Sessions onto their YouTube channel. Dive into the archive here.
Sportsman's Club's backyard BBQ series is back for another year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. Logan Square mainstay Lula Cafe will be behind the grill for Labor Day weekend.
They say that there's nothing more American than apple pie, but we're of the opinion that the most patriotic food of all is the chicken wing. Soaked in a variety of different sauces (from classic buffalo to Asian ginger, spicy garlic and honey chili), it's a versatile dish that has become a national staple. In this two-day fest, WingOut Chicago celebrates the venerable chicken wing, inviting cooks from Jake Melnick's, Smoke Daddy, Harold's Chicken and more to put their spin on the dish. General admission includes entry and access to live entertainment, with the option to purchase a la carte wings and beverages. Opt for VIP tickets for early entry, all-you-can-eat wings and a drink package.
Wind down from the Labor Day festivities by flexing your brain and tipping back a few drinks at aliveOne. Guests can enjoy special beer-and-shot combos and free music trivia hosted by Whaddayaknow Trivia. After trivia wraps up, decompress from the holiday weekend with a few rounds of free pool.
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