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, movies under the stars, music and food festivals, cocktails at the beach, and so much more. Check out top events and things to do over Labor Day weekend in Chicago.  

Check out a music festival

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 under the stars in Millennium Park, experience authentic Latinx music and culture in Pilsen, dance the night away at a new house music festival, and more.

  • ARC Music Festival: This new fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.
  • Chicago in Tune: This new music festival will feature free and ticketed events at venues around the city and iconic Millennium Park.
  • ¡Súbelo!: Head to the vibrant Pilsen neighborhood for this celebration of Latinx music and culture.
  • Millennium Park Music Series: Grab a spot on the grass and enjoy a free performance by contemporary Indigenous performers.
  • 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.

Fill up at a food fest

Are food festivals more your style? We’ve got those too! Get a taste of our diverse dining scene at these Labor Day weekend food events. Dig into the best local burgers, fill up on tacos from a street vendor, and indulge in traditional Polish fare.

  • Roscoe Village Burger Fest: Find the best burger in the city at this local favorite, all while enjoying live music and cold drinks.
  • Food Truck Fest: Head to Daley Plaza to sample fare from a wide variety of local food trucks.
  • Maxwell Street Market: This Sunday market is a Chicago tradition with an eclectic mix of handmade crafts, live music, family fun, and some of the best street food in Chicago.

Take a boat cruise


Set sail on one of Chicago’s famous boat cruises. 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 Riverwalk restaurants and bars are open for just a little longer, so make your reservations now.

Catch a baseball game


The regular season might be winding down, but you still have time to catch the Chicago Cubs play at historic Wrigley Field. One of the oldest MLB stadiums in the country, seeing a game at Wrigley is truly a bucket list experience. Grab a seat in the sunny bleachers, watch from the surrounding rooftops, or just pull up a bar stool and catch the game from one of the neighborhood’s many sports bars. Afterward, spend some time exploring lively Wrigleyville.

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.

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 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

Immersive Van Gogh Exhibit

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 modern art to fascinating ancient history and beyond. Check out a few can’t-miss exhibits in Chicago right now:

  • Immersive Van Gogh Exhibit at Germania Club: Submerge yourself within Van Gogh’s most iconic paintings at this unique immersive showcase of his work
  • The Art of Banksy at 360 N. State St.: Billed as the largest Banksy exhibit ever assembled, the show will feature more than 80 works by one of the world’s most mysterious artists.
  • Marvel: Universe of Super Heroes at Museum of Science and Industry: Celebrate 80 years of Marvel by visiting this interactive exhibit of more than 300 costumes, props, sculptures, artifacts, and displays.
  • Frida Kahlo: Timeless at the McAninch Arts Center: This comprehensive show includes original works and historic artifacts, including Kahlo’s clothing, photos from her life, and a Kahlo-inspired garden.
  • Sky Shows at Adler Planetarium: Get a front row seat to the mysteries of space in the Adler Planetarium’s iconic dome theater.

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 soak in some skyline views from the lakefront.

Explore Navy Pier

An outdoor concert at Navy Pier
Photo by James Richard IV

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:

Be 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 African American labor movement.

Fittingly, Labor Day weekend marks the grand opening of the Pullman National Monument and State Historic Site. The public will be welcome to tour the brand new Visitor Center at Pullman National Monument and the adjacent grounds of the State Historic Site. The weekend will be filled with free activities, live music, and food trucks.

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 specials 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!