Round out summer in Chicago with a long weekend of outdoor fun and unique local events. Catch the last wave of summer warmth by cruising Chicago’s majestic waterways by boat or kayak, enjoying open-air dining on a rooftop or patio, cycling along scenic lakefront paths, experiencing free live music under the stars at the Chicago Jazz Festival, and much more.
Make the most of Labor Day weekend in Chicago with these top activities and events.
Attend a Labor Day weekend music festival
Labor Day weekend in Chicago gathers all the best parts of summer — live music, street food, and the great outdoors — for a final celebration of the season before fall rolls in.
Immerse yourself in the city’s dynamic soundscape by attending Chicago’s annual music festivals. Between soulful jazz drifting through Millennium Park and electrifying house beats pulsing in Union Park, here are a few highly anticipated Labor Day weekend music fests:
- Chicago Jazz Festival: Bask in smooth tunes at this free lakefront event at Pritzker Pavilion, featuring a diverse roster of jazz talent, from emerging artists to genre-defining legends.
- ARC Music Festival: Honoring Chicago’s house music legacy, Union Park comes alive with a high-energy dance party that carries the rhythm late into the night.
- North Coast Music Festival: Experience a powerhouse lineup of electronic dance music, hip-hop, and rock acts alongside immersive art and food stalls.
Celebrate community and culture at a neighborhood festival
Discover the spirit of Chicago’s vibrant neighborhoods by exploring these community celebrations highlighting local culture, music, and food:
- Taste of Polonia Festival: Celebrate Chicago’s Polish roots in Jefferson Park with authentic culinary delights, dance and music performances, casino games, dedicated kid-friendly festivities, and more.
- WingOut Chicago: At Gallagher Way in Wrigleyville, feast on a variety of flavorful wings from local vendors while live music and lighthearted competitions fuel the fun.
- Sky Blue Music and Culture Festival: Head to Woodlawn for live entertainment, artist showcases, tasty dining options, and engaging community activations and panels.
Festival season in Chicago never ends! Explore our year-round guide to top festivals in Chicago.
Bike down Lake Shore Drive
Cruise into Labor Day weekend with unbeatable scenery and the freedom of the open road. Bike the Drive is back on Sunday, Aug. 31, giving you a chance to ride down Chicago’s iconic lakefront roadway.
This once-a-year event clears the way for thousands of riders to take over the 30-mile loop. With miles of open road and uninterrupted lake views, it’s one of the city’s most scenic rides. No bike? No problem. Rentals are available and ready to roll.
Attend the Chicago Labor Day Parade
The annual Chicago Labor Day Parade and Eddie Fest returns to Pullman, a historic neighborhood deeply connected to the origins of the country’s labor movement.
Along with a captivating performance by the South Shore Drill Team, the Labor Day parade features dozens of colorful floats courtesy of community groups, unions, elected officials, and businesses.
After the parade, Eddie Fest follows with all-ages entertainment and activities, in addition to bounce houses, food and craft vendors, and live music, including a DJ set.
While you’re there, delve into the history behind Pullman by taking a self-guided tour of the national monument or join the monthly First Sunday Walking Tours.
Established in the 19th century, Pullman National Historical Park started as a planned industrial town for workers of an upscale railcar manufacturer. Over time, this district became central to shaping labor rights in the U.S.
Today, it’s preserved as a National Historic Landmark with remarkable architecture and stories that reflect its complex legacy. Pullman’s brick homes and factories still stand, offering a glimpse into a formative era of Chicago’s past.
See the sights aboard a Chicago boat cruise
Mild temperatures and a steady breeze make Labor Day weekend in Chicago the perfect time to set sail on a boat tour. Cruises along the river and lakefront provide a front-row seat to the city’s architecture, shoreline, and late-summer glow.
Choose from tours that dive into the action with fast-paced speedboat rides or keep the occasion light with local history, tiki-themed drinks, and sunset views. Check out some of the city’s most popular cruises and boat tours:
- Explore Chicago’s architecture with Wendella Tours & Cruises
- Board the iconic First Lady for the Chicago Architecture Center River Cruise
- Embark on theArchitecture River Tour with Shoreline Sightseeing
- Savor good eats on the Brunch Cruise on Lake Michigan with City Cruises
- Buckle up for an adventure on Chicago Seadog Extreme Thrill Ride
- Sip tropical cocktails at the tiki bar aboard Island Party Boat
Or if you prefer to be your own captain, rent pontoons, retro boats, donut boats, and more with Chicago Boat Company.
Follow our guide to Chicago boat tours to navigate Lake Michigan and the Chicago River with ease.
Wander the Chicago Riverwalk
The Chicago Riverwalk is a local favorite year-round, but it hits a sweet spot over Labor Day weekend. Warm days and cooler nights mean it’s a must-visit destination for outdoor dining or a leisurely stroll.
Make time to stop at one of the many riverside restaurants and bars, admire public art like the mesmerizing nighttime Art on THE MART, and hop on a boat tour right from the river’s edge.
Watch one of Chicago’s iconic sports teams
Rally behind your favorite team at a live game. Check the schedule and snag tickets while you can — Labor Day weekend games tend to draw a crowd. Here’s a look at a few of the matchups:
- Chicago White Sox: Get ready for a series of exciting games as the Chicago White Sox go head-to-head with the New York Yankees at Rate Field on Aug. 29 – 31.
- Chicago Cubs: Wrigley Field, one of the nation’s most storied ballparks, is setting the stage for the Chicago Cubs’ showdown with the Atlanta Braves on Monday, Sept. 1.
See the fireworks at Navy Pier
The city’s lakeside playground Navy Pier delivers old-school fun along with postcard-worthy views of the cityscape. Plus, this iconic landmark dazzles the night sky with free fireworks displays all summer long. Catch this season’s final fireworks show on Saturday, Aug. 30.
When visiting the pier, look forward to cocktails and shareable bites at Offshore Rooftop — the world’s largest rooftop bar — after taking a ride on the Centennial Wheel or one of many attractions at Pier Park. For more ideas, check out more things to do at Navy Pier.
Bike or walk the Lakefront Trail
The Lakefront Trail weaves through many of Chicago’s lakeside neighborhoods, including Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, and Hyde Park. The trail provides convenient access to parks, museums, and scenic waterfront restaurants.
Bikers, skaters, runners, and pedestrians share the nearly 20-mile route as it hugs the edge of Lake Michigan, connecting urban areas with quiet pockets of nature. Lace up your sneakers or rent a Divvy bike, and follow the lake wherever it leads.
Visit a Chicago museum
This Labor Day weekend, uncover massive dinosaur skeletons and an ancient Egyptian tomb at the Field Museum, located on Chicago’s famous Museum Campus.
Families with kids love to interact with hands-on exhibits at the Griffin Museum of Science and Industry, tucked away within Museum Campus South in Hyde Park.
No matter if you prefer reflecting on thought-provoking works at the Museum of Contemporary Art or influential literature at the American Writers Museum, there are endless opportunities for discovery at must-see Chicago museums.
Hit the beach
From centrally located North Avenue Beach to dog-friendly Montrose Beach to historic South Shore Beach, Chicago is brimming with more than two dozen free beaches that make for a perfect lakeside retreat during a long holiday weekend.
On a sun-soaked afternoon, beach-goers can meander down the shore, cool off with a swim, play beach volleyball, rent kayaks or jet skis, and lounge on the sand. And when it’s time to recharge, swing by a beachfront bar for refreshments.
Check out our Chicago beach guide to find the perfect sandy spot for you.
Rent a kayak or paddleboard
Kayaking in Chicago is one of the most unique ways to experience the sights and sounds of the city, while taking in gorgeous views from Chicago’s many waterways.
Cruise through the heart of downtown with Urban Kayaks, which offers kayak tours and rentals right from the Chicago Riverwalk. Or check out Bobby’s Bike Hike to rent tandem kayaks or paddleboards to glide along the scenic lakefront.
For a unique paddleboarding experience, check out Neon Paddle. These evening tours use motorized, lit-up paddleboards, so you can enjoy the sights without having to paddle.
Enjoy outdoor dining in Chicago
Toast to summer’s final stretch with open-air dining featuring unforgettable flavors and scenic surroundings. Ease into Labor Day weekend with a leisurely brunch on a charming garden patio, then unwind with a handcrafted cocktail at a chic rooftop bar.
You’ll find plenty of patio and rooftop dining options throughout Chicago’s bustling downtown and vibrant neighborhoods. After all, exceptional food tastes even better al fresco — find out where to go with our outdoor dining guide.
Raise a glass at a local brewery
As one of the nation’s leading craft beer hubs, Chicago boasts a wide range of taprooms offering an impressive variety of brews. From smooth lagers to hop-forward IPAs and everything in between, the top Chicago taprooms are serving up quality pours.
Choose from tried-and-true favorites to bold and experimental pints featuring botanicals and foraged ingredients. Sip your way through the city by uncovering Chicago brewery itineraries by neighborhood, like Malt Row in Ravenswood or the West Side’s Chicago Brewing District.
