The Haute Seeker

16 of the Best Labor Day Weekend Events in Chicago

As Labor Day weekend approaches, Chicagoans are gearing up for a long weekend filled with fun events and activities. From music festivals to food fairs and everything in between, there’s something for everyone to enjoy.

If you’re looking for the best Labor Day weekend events in Chicago, look no further. In this post, I’ve found the best Labor Day weekend events in the city, so you can make the most of your holiday weekend. Whether you’re a local or just visiting, these events are sure to leave you with lasting memories.

So, read on for the best of what Chicago has to offer!

Why Do We Celebrate Labor Day?

close up photography of american flag
Photo by Brett Sayles on

Just like Memorial Day is the unofficial start of the summer, Labor Day is often seen as the end of the summer season. So how did the holiday get it’s start? According,Labor Day is an annual celebration of the social and economic achievements of American workers. The holiday is rooted in the late nineteenth century, when labor activists pushed for a federal holiday to recognize the many contributions workers have made to America’s strength, prosperity, and well-being.

Chicago Weather During Labor Day Weekend 2023

With Labor Day weekend fast approaching, we’re all eagerly holding on to the warm and sunny weather before the fall chill breezes in. Whether you’re looking to hit the beach, attend a festival, or simply explore the city, the forecast calls for ideal conditions with temperatures ranging from the low 70s to high 80s. So go ahead and make the most of it – there’s never been a better time to experience the Windy City!

Things to Do Labor Day Weekend Chicago

Labor Day weekend in Chicago is packed with exciting and enjoyable activities. Check out some of the top things to do in the city during this time.

  1. Eat, drink, and shop like a local—we’ve got a list of all of their favorite spots.
  2. Snag a seat on a popular patio in one of Chicago’s coolest neighborhoods.
  3. Explore a Chicago museum and see what’s new from the past, present, or future. Check out this roundup of the best museum exhibitions to see in 2023.
  4. Take a stroll on the Chicago Riverwalk for an authentic summertime Chicago experience.
  5. Catch the Chicago White Sox and Cubs as their regular season comes to a close, as well as the Chicago Sky playing at home. Additionally, don’t miss the Chicago Football Classic featuring historically Black colleges at Soldier Field.
  6. Check out a neighborhood festival that celebrates summer and welcomes fall—here are a few of our favorites.
  7. Take a dip in a rooftop pool before they close for the season.
  8. Catch the final summer fireworks show at Navy Pier for free.
  9. Fuel your long weekend with Labor Day brunch specials from Old Town Pour House, and Sweetwater Tavern & Grille, The Hampton Social, and more.
  10. Discover the lesser-known American history of Chicago with a guided tour of the city.
  11. Load up on the freshest apples and sweets at a nearby Chicago U-pick farm before everyone else.
  12. Enjoy non-stop dancing at Labor Day weekend day parties happening throughout the city—from beach parties to popular neighborhood nightlife hot spots.

Labor Day Events Around Chicago

There are plenty of activities, festivals, and annual events that take place during Labor Day weekend. Check out this list of the unique events taking place over the holiday weekend.

2023 Bike the Drive

Sunday, September 3rd // 6:30 a.m. – 10:30 a.m., Festival 8 a.m. – 12:30 p.m

Cost: $18 – $84

Ever dreamed of having Lake Shore Drive all to yourself? Now you can—kind of. The annual Bike the Drive event is a recreational, non-competitive bicycle ride held each on DuSable Lake Shore Drive. The event benefits bicycling advocacy work in the region by the Active Transportation Alliance.

Ziba Market Presents: The 2nd Annual Bazaar at Kimball Arts

Monday, September 4th // 1 p.m. – 7:00 p.m.

Cost: Free

Load up on art, apparel, vintage, and home goods at the 2nd annual Ziba Market. With over 30 vendors selling everything from housewares to candles, you’re sure to find something you love. Plus, there are fun activities like tattoos, aura readings, and tooth gems. Shop, sip, savor, and enjoy sounds by live DJs during this Labor Day weekend event!

Chicago Jazz Festival

Thursday, August 31st – Sunday, September 3rd

Cost: Free Admission

The free Chicago Jazz Festival returns with performances celebrating all forms of jazz in Millennium Park, at the Chicago Cultural Center, and citywide. The annual Labor Day weekend tradition promotes all forms of jazz through free, high-quality music programming. The festival showcases Chicago’s local talent alongside national and international artists to raise awareness and appreciation for one of the city’s most beloved art

Chicago’s Labor Day Parade & Eddie Fest

Saturday, September 2nd // 12:00 p.m. – 6:00 p.m.

Cost: Free Admission

Make and celebrate history during the first-ever Labor Day Parade with the Chicago Federation of Labor at the Historic Pullman National Historical Park. Official records vary, but one can be certain that Chicago’s first Labor Day Parade took place in the 1880s. Since that time, parades have varied from place to place but have finally found a new home in the Pullman Historic District, which has been developing and highlighting its ties to the Chicago labor movement and labor history over the past few years.


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