The Best Outdoor Events Hitting Chicago over Labor Day Weekend

Chicago Jazz Festival ampitheater with crowd sitting in grass Shutterstock
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There’s no better place to be than outside during Labor Day weekend in Chicago, so we’ve rounded up the best outdoor family-friendly festivals and activities to soak up the sun

Labor Day weekend can be a magical time in Chicago. Summer breaks are over and kids have just returned to school, so it serves as one last chance for some carefree summer fun. Some will head out of town, but many of us locals know that there is no better time, and no shortage of fun, to have right here in the Windy City. Festivals are plentiful this time of year, the lake has finally reached a comfortable temperature, and if the sun is shining, people will be found outdoors soaking it up in any way they can.

Among the outdoor fun to be had this Labor Day weekend—for the foodies, the audiophiles, and adventure junkies alike—there is a little something for everyone and every budget. So grab your sunscreen, and your family, and head on out to savor a long holiday weekend. If you haven’t already, you’ll discover what makes this such a special time in the city.

The Great American Lobster Fest
The Great American Lobster Fest celebrates its seventh year at Navy Pier. Enjoy live lobster flown in fresh from the cold waters of the East Coast, live music performances, family-friendly games, unique craft shopping, and cold beverages. Picky eaters need not worry: they’ll also have plenty of dessert and non-seafood items to please the whole family! The festival grounds are open to the general public to enjoy live music and many different food, drink, and craft vendor options. Do note that no lobster meals are included for walk-up guests, and VIP or special meal experiences are a separate fee.

When: Sep. 2-4
Navy Pier
600 E. Grand Ave.
Online: lobsterfest.com

Related: The Best Ways to Use Up Every Last Drop of Summer in Chicago

North Park Neighborhood Artisan Market
Whether you are looking for a cool t-shirt, a toy or souvenir your family has not seen before or a one-of-a-kind collectible for your home, shopping in Chicago is more dynamic and delightful at Navy Pier. Learn about the different neighborhoods of Chicago and their talented residents. Meet local artists, see their craft and learn their stories. While you are at the Pier you can find plenty of things to do as a family—from splashing in the fountain at Polk Bros park to climbing aboard the ferris wheel for a bird’s eye view of the city and lake.

When: Sep. 2-4
Navy Pier
600 E. Grand Ave.
Online: navypier.com

Chicago Jazz Festival
The Chicago Jazz Festival is a Labor Day weekend tradition that 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 forms.

When: Sep. 2-4
Millennium Park
201 E. Randolph St.
Online: jazzinchicago.com

Nashwood
Slip on your boots and don your cowboy hats and head to Downtown Highwood for three days of live country, bluegrass, southern rock music and some tasty Southern inspired food and drinks! This event is free and for all ages with a family-friendly lineup and activities on both Friday and Saturday.

When: Sep. 2-4
Highwood Ave. & Green Bay Rd.
Highwood, IL
Online: celebratenashwood.com

Lincoln Square Greek Fest
Opa! Celebrate the end of summer at St. Demetrios Greek Orthodox Church over Labor Day weekend for their annual Lincoln Square Greek Fest. Enjoy Greek food, delicious pastries, loukoumades (Greek honey puffs), NORTHSIDE’s performance on Friday, Greek dance troupes, and the Hellenic marketplace.

When: Sep. 2-5
St. Demetrios Greek Orthodox Church
2727 W. Winona St.
Online: lincolnsquaregreekfest.com

Taste of Polonia Festival
Did someone say pierogi? For four days, you can enjoy a true cultural experience that includes nonstop live music, dance performances, authentic Polish food and beer, exhibitions, local merchants, a casino, beer garden, a kids stage and area filled with great activities and much much more! The largest Polish festival in the US is a Labor Day weekend tradition in Chicago.

When: Sep. 2-5
5216 W Lawrence Ave.
Online: tasteofpolonia.com

Fireworks at Navy Pier
Catch the final fireworks show of the summer over Labor Day weekend. You can see the fireworks from Navy Pier, or find a vantage point along the lake shore if you want less of a crowd and a little space to spread out. You can also check out one of the many options to watch the show aboard a boat!

When: Sep. 3
Navy Pier
600 E Grand Ave
Online: navypier.com

Related: Discover the Not-So-Obvious Spots to Hike, Camp & Fish Near Chicago

Bike the Drive
Grab your helmets and set your morning alarms for a Sunday morning ride along DuSable Lake Shore Drive—from the neighborhoods of Edgewater to Bronzeville—to explore Chicago in a new way while spending time being active outdoors together. While the main festival is located in iconic Grant Park, you are able to begin riding from any of the five entry points along the course and you can choose to do the full 30-mile loop, or you can stop, or change direction at any of the checkpoints and rest stops along the way. You can register in advance for this event to avoid paying “same day” pricing. This event does support the Active Transportation Alliance which works to enhance walking, biking, and public transportation conditions throughout Chicago.

When: Sep. 4
DuSable Lake Shore Drive (between Bryn Mawr Ave. and Oakwood Blvd.)
Online: bikethedrive.com

Art on theMART
Mesmerizing and beautiful since its debut in 2018, this is something worth seeing at least once in your life, but with a seasonally changing schedule of shows, you can see it over and over in a year if you like! In fact, Labor Day weekend is a great time to see the current shows before new ones debut September 8th. Art on theMart is the largest permanent digital art exhibit in the world, covering over 2 acres of the building’s south facade. Pack a picnic and use public transportation to save yourself the hassle (and expense) of parking.

When: Nightly at 9 p.m.
Chicago Riverwalk (between Lake & Wells)
Online: artonthemart.com

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