Summer in Chicago may be winding down, but Labor Day weekend is full of ways to enjoy the remaining sunshine and warm weather. Celebrate the end of the season with scenic boat cruises, dinner on a patio, music under the stars (including the iconic Chicago Jazz Festival), exhilarating live sports, cocktails at the beach, and so much more. Plus, it’s the perfect time to visit Chicago’s Pullman National Historical Park, which played a central role in the country’s labor movement. Check out just a few of the top events and things to do over Labor Day weekend in Chicago.  

Attend a festival

Summer may be winding down, but festival season is still going strong.

You can’t do Labor Day in Chicago without checking out one of the city’s annual music festivals. This year, the weekend includes an exciting schedule of fests — catch jazz legends playing free shows in Millennium Park, dance the night away at a house music festival, and more.

  • Chicago Jazz Festival: The oldest of Chicago’s free lakefront music festivals boasts an incredibly diverse lineup in the heart of the loop.
  • ARC Music Festival: This immersive fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.
  • 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.

If you’re looking to explore Chicago’s vibrant neighborhoods, these popular neighborhood fests celebrate the city’s diverse food, music, and arts scenes.

  • African Festival of the Arts: This culturally immersive event recreates an African village in Washington Park, with live music, yoga, dancing, vendors, and culinary delights.
  • Taste of Polonia Festival: Celebrate Chicago’s Polish heritage with live music, a casino, a beer garden, a kids area, and of course, endless Polish food and beer.
  • West Loop Art Fest: Come browse six blocks of unique art across a range of mediums, plus live music and wine tastings.
  • Sky Blue Music and Culture Festival: This Woodlawn festival will feature musical performances, artist showcases, community activations, a food court, and more.

Explore more: Check out our guide to top festivals in Chicago all year round.

Bike down Lake Shore Drive

Bike the Drive on Lake Shore Drive
Bike the Drive on Lake Shore Drive

Enjoy a scenic ride down Chicago’s stunning DuSable Lake Shore Drive, which is shut down to cars just one day each year. Bike the Drive on Sunday, Sept. 1 features a 30-mile loop on the iconic road, inviting bikers to enjoy a long or short ride while taking in views of the lake and city skyline. No wheels? No problem. Bike rentals are available.

Step inside Chicago history

Pullman National Monument

The Pullman Historic District, the city’s first National Historical Park, was built from scratch in 1865 as a planned industrial town for employees of a luxury railcar manufacturer. Today, Pullman is known for its striking architecture and for its role in the early labor movement.

Honor the history of Labor Day and learn more about this fascinating community by joining the First Sunday Walking Tour on Sept. 1 for a guided look at the National Monument and the surrounding area. The neighborhood will also be hosting the annual Chicago Labor Day Parade and Eddie Fest.

Take a Chicago boat tour or cruise


Set sail on one of Chicago’s scenic boat cruises on our two sparkling waterfronts. Choose from informative architecture tours, fast-paced speedboat rides, unforgettable dinner cruises, tiki-themed party boats, sunset and fireworks cruises, and more. Here are just a few boat cruises happening on the water this Labor Day weekend:

Check out our guide to Chicago boat tours on Lake Michigan and the Chicago River.

Wander 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. The popular waterfront restaurants and bars are open for just a little longer, so make your reservations now.

Catch a sports game

If you’re a sports fan, Labor Day weekend is a great time to visit Chicago. Check out when you can see some of the city’s top teams play all around the city.

  • Chicago White Sox: The regular season might be winding down, but you still have time to catch the Chicago White Sox play The Mets at Guaranteed Rate Field from Aug. 30 – Sept. 1.
  • Chicago Cubs: The Chicago Cubs will be in town for the holiday, playing the Pirates during a night game on Monday, Sept. 2. Their ballpark, Wrigley Field, is one of the oldest and most iconic stadiums in the country.
  • Chicago Sky: The Chicago Sky will play the Indiana Fever in a much-anticipated face-off on their home court at the Wintrust Arena on Friday, Aug. 30.

See the fireworks at Navy Pier

NYE Fireworks at Navy Pier

One of the city’s top attractions is Navy Pier, a waterfront stretch of rides, restaurants, entertainment, and more. The Pier is known for its spectacular summer fireworks displays. Don’t miss the last show of the season on the evening of Saturday, Aug. 31.

While you’re there, take a spin on the iconic Centennial Wheel, grab a drink at Offshore (the largest rooftop bar in the world), and check out more things to do at Navy Pier.

Bike or walk the Lakefront Trail

Biking down Lakeshore Drive on Divvys
Clayton Hauck for Choose Chicago

Chicago’s gorgeous Lakefront Trail stretches almost 20 miles along Lake Michigan, offering stunning skyline views and connecting you to many of Chicago’s waterfront neighborhoods, including Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, and Hyde Park. The scenic trail is a popular place for walking, biking, running, and rollerblading. Rent a Divvy bike if you want to cover the most ground, and make sure to leave time to stop at one of the many waterfront restaurants.

Visit a museum

Art Institute of Chicago
Art Institute of Chicago

Which Chicago museum is on your bucket list? The long weekend is the perfect time to visit one of the city’s world-class museums that let you immerse yourself in everything from avant garde works at the Museum of Contemporary Art to fascinating ancient history at the Field Museum to interactive exhibits at the Griffin Museum of Science and Industry and beyond.

Check out our guide to Chicago’s Museum Campus, Museum Campus South, or explore museums throughout the city.

Hit the beach

Abel Arciniega :: @tequilagraphics

Labor Day weekend marks the last days of beach season in Chicago, so make sure to pack your swimsuit and plan some time to enjoy our gorgeous lakefront. Swim, tan, play volleyball, or head to a nearby beachfront bar to enjoy a cold drink with your toes in the sand. Check out our beach guide on the best places to soak up the sun before summer is over.

Rent a boat or kayak

Be a captain for a day with your very own boat rental. It’s the perfect way to get out on the water, whether you’re kicking back on a yacht or paddling your own kayak.

Charter a private yacht with Free Spirit Yacht Cruises for a luxurious Labor Day experience. Island Party Boats offers boat rentals that include a captain, booze, and even a waterslide. Or cruise along the river in an affordable, eco-friendly electric boat from Chicago Electric Boat Company.

A retro boat from Chicago Electric Boat Compant
Photo courtesy Chicago Electric Boat Company

If you’d rather work up a sweat, rent a kayak with Urban Kayaks on the Chicago Riverwalk and paddle through the heart of the city, past the bustling Riverwalk and some of the city’s most iconic buildings. Or head to the lakefront to rent a kayak or join a guided tour from Bobby’s Kayak Company and enjoy the breathtaking views of the skyline and some of the city’s can’t-miss landmarks.

Explore outdoor dining in Chicago

Patio weather in Chicago comes and goes quickly. Enjoy one of the best al fresco weekends with an outdoor brunch on an enchanting garden patio or craft cocktails at a rooftop bar with skyline views. Check out our outdoor dining guide, with some of the best patios all around Chicago.

Visit a local brewery

Drinking beer on the ERIS patio
Sip house-made cider from ERIS Brewery in Irving Park.

Chicago is one of the nation’s best craft beer cities. We’re home to a mind-boggling number of cool tap rooms, specializing in everything from foraged botanical beers to experimental microbrews. Check out one of the city’s brewing hot spots like well-established Malt Row in Ravenswood or the up-and-coming Chicago Brewing District on the West Side. Here’s our guide on top Chicago tap rooms and Chicago brewery itineraries by neighborhood.