How to Spend Labor Day Weekend in Chicago

Though Labor Day is a national holiday, unlike most other major holidays, Labor Day doesn’t come with many predefined traditions.  For most, this day that celebrates the contributions of the American worker, it’s simply a much-needed extra day off from the grind and an always coveted three-day weekend.  So, don’t waste a single moment of this celebration that marks the end of summer, and hit the town to send off the season in style.

What to Look Forward to on Labor Day Weekend in Chicago

Here are just a few ways you can spend your long weekend:      

Navy Pier

Everyone knows Navy Pier is the quintessential Chicago attraction.  It’s great to visit any time of the year, but it’s especially exciting throughout the summer season.  So, get your last summer hurrah in before the chill moves in. Don’t miss the Summer Fireworks Display on September 1st at 10:15 p.m.  And, be sure to come out for Music on the Lake all Labor Day weekend-long for some free live music and dancing.  

The Great American Lobster Fest at Navy Pier

Now in its 5th year, you can experience the Great American Lobster Fest at Navy Pier from August 31st – September 2nd, and trust us, this is one event you won’t want to miss!  It’s the largest lobster and seafood festival in the Midwest, boasting exceptional lobster and seafood dishes, live performances, family games, arts and crafts and more.

Chicago Jazz Festival

Head to Millennium Park and the Chicago Cultural Center to experience this legendary lakefront music festival from August 29th – September 2nd.  It’s a longstanding Chicago Labor Day tradition and one of the best ways the city celebrates the end of summer.  Enjoy free live music performances that showcase all varieties of jazz, featuring both local and even international musicians.

North Coast Music Festival

Experience the famous North Coast Music Festival at Union park August 31st – September 2nd, as it brings together people from all walks of life and artists of every genre.  Whether you’re into folk, rock, or hip hop, all of your favorite artists will take the stage.  Some of the headliners of this year’s lineup include Axwell X Ingrosso, Miguel, Midnight Conspiracy Cover Band, DJ Snake and more.

Architecture River Cruise

What better way to spend the long weekend than by getting to know your town a little better?  Explore Chicago’s beautiful and unique architecture aboard a Shoreline river cruise. Set sail down all three branches of the Chicago River, and see some of the most iconic buildings that make up our gorgeous skyline, including sights designed by famed architects Skidmore Owings Merrill, Mies van der Rohe, Bertrand Goldberg and more.  There’s just no better place to view some of the world’s most dazzling buildings and structures.

Art Institute of Chicago

If you want to infuse your mini vacation with a little culture, spend a day at the world-famous Art Institute of Chicago.  The award-winning museum is filled with diverse collections of amazing works of art and historical artifacts. Take the whole family, and travel through time for the ultimate vacation adventure.

Brookfield Zoo

A day spent at the Zoo is never a bad idea!  Spend the end of summer celebrating in the sun, and explore the city’s largest zoo with its 216-acre park.  See all of your favorite exhibits, from the Big Cats, to the Great Bear Wilderness, to the Living Coast, Seven Seas and more.   

Go for a Bike Ride

Soak up the last of the summer sun by spending an entire day outdoors.  Rent a bike, and roam the great urban outdoors. You can start at Navy Pier, and pedal along the many miles of waterfront trails.  There is so much to see and do, you’ll just be sorry you didn’t do it sooner!

SkyDeck Chicago

Let your inner shutterbug out with a trip to the top of the Willis Tower for some stunning views of the Chicago skyline.  Take a step out onto The Ledge, if you dare, for an unobstructed view of the Windy City from the glass lookout. This is one of those excursions every Chicago native must take at some point, so why not use the long weekend to check it off your bucket list!    

There are so many fun things to do around Chicago to celebrate Labor Day and the official end of summer.  So, get your family and friends together, and start planning your holiday weekend itinerary.


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