We made it, y’all—Labor Day weekend, summer’s bittersweet swan song, has arrived. And it comes with no shortage of ways to soak up the season’s final long, sunny days. Feeling overwhelmed by the endless possibilities? Fear not—we’ve scoured the city’s packed calendar to bring you the very best festivals, events and activities to make the most of your three-day weekend.
Chicago Jazz Festival
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. This year's headliners include composer Esperanza Spalding, saxohponist Ari Brown and drummer Greg Fundis. Visit the Chicago Jazz Festival webpage for the full lineup and schedule.
Be awed by the final Navy Pier Fireworks show of the year
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.
Catch a movie at the last-ever Music Box Garden series
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 screening Monday, September 1, through Thursday, September 4.
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Enjoy rooftop views at Cindy’s
A crown jewel sitting atop the Chicago Athletic Association, Cindy’s is a go-to for entertaining out-of-towners and summer fun. The rooftop restaurant and bar offers unparalleled views of the city, with an expansive look at Millennium Park and the Lake. Don’t leave without catching a glimpse of an original Andy Warhol portrait overlooking the bar—a portrait of Cindy Pritzker, namesake of the bar and mother of the hotel’s owner, John Pritzker.
Admire the blooms at the Chicago Botanic Garden
Through meticulously planted gardens and nature-inspired art installations, Patterned by Nature—the Chicago Botanic Garden’s latest exhibition—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.
Bike down Lake Shore Drive
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)—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.
Decorate a cake with some pastry pros
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.
Soak up some rays at Rainbow Beach and Park
Part of the 142-acre Rainbow Park, this South Side beach sits next to one of Chicago’s oldest public gardens, the Rainbow Beach Victory Garden. Amenities are abound here, including a concessions stand, volleyball and handball courts, a community garden and more. The northern edge of this beach is also home to the 9.2-acre Rainbow Beach Dunes, a natural area managed by the Chicago Park District that hosts plants and wildlife native to the shores of Lake Michigan.
Find your sea legs with Kayak Chicago
After a few quick lessons covering how to balance and steer your kayak, you’ll be able to push off from the dock and start exploring the Chicago River and Lake Michigan. Kayak Chicago charges an hourly rate (prorated to the quarter hour after the first hour), so you’re able to stay on the water as long as you like—or you can pay a flat fee to rent a kayak for an entire day. Tours are also available and are on the lengthier side (about three hours), with guided excursions that highlight Chicago architecture or simply allow you to navigate the river at night.
Chow down at WingOut
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.
Bonus: Chicago Labor Day Parade & Eddie Fest
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 to celebrate the city’s working class 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.