Summer in Chicago may be coming to an end, but Labor Day weekend is full of ways to enjoy the final days of sunshine and warm weather. Celebrate the end of the season with boat cruises, dinner on a patio, music under the stars, exhilarating live sports, cocktails at the beach, and so much more. Check out top events and things to do over Labor Day weekend in Chicago.  

Catch some live music

You can’t do Labor Day in Chicago without checking out one of the city’s annual music festivals. This year, the weekend is packed with a diverse line-up of fests — catch a free concert 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 new 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.

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 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.

Take a boat cruise


Set sail on one of Chicago’s famous 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’s 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.

Explore 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.

Cheer for the home team

The regular season might be winding down, but you still have time to catch the Chicago White Sox play. They’ll be facing off at Guaranteed Rate Field all weekend long. Afterward, spend some time exploring the lively Bridgeport neighborhood.

The Chicago Cubs will be in town for the holiday, playing the Giants on Monday, Sept. 4. Their ballpark, Wrigley Field, is one of the oldest and most iconic stadiums in the country — truly a bucket-list activity.

Eat outdoors

Patio weather in Chicago comes and goes quickly. Enjoy one of the last 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.

Wander 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 EdgewaterUptownLakeviewLincoln ParkSouth LoopBronzeville, and Hyde Park. The 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 cutting-edge works at the Museum of Contemporary Art to fascinating ancient history at the Field Museum to interactive exhibits at the 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 end of beach season in Chicago, so make sure to pack your swimsuit. 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 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 and eco-friendly electric boat from 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 their Monroe Harbor location to hop on a kayak or paddleboard to soak in some skyline views from the lakefront.

Explore Navy Pier

NYE Fireworks at Navy Pier

It’s one of the city’s most popular attractions for a reason. Navy Pier has plenty of events and activities for locals and visitors alike, from free outdoor concerts to the world’s largest rooftop bar. Check out top things to do on the Pier during Labor Day weekend:

Explore a part of Chicago history

Pullman National Monument

The Pullman Historic District, the city’s first and only National Monument, was built from scratch as a planned industrial town designed by luxury railcar tycoon George Pullman for his employees. Today, Pullman is known for its striking architecture and 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 for a guided look at the national monument and the surrounding area.

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. For instance, 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.

Stay the night

Sophy Hotel in Hyde Park

Looking for a staycation or a weekend getaway? Tons of Chicago hotels are offering special deals and discounts for the long weekend. You can snag everything from free room nights to complimentary breakfast and room upgrades to attraction passes and special family packages. Don’t miss out on making the final weekend of summer a truly memorable one!

Explore more: Check out our guide on the best things to do in Chicago in the fall.