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August 2023

21 Best Labor Day Weekend Events in Chicago

Credit: Star Events

Ah, three-day weekends! Whether you're traveling to Chicago from out-of-town or you're a local looking to take advantage of the last days of summer, we've got you covered! From music festivals to bike rides, there's something for everyone to enjoy. Check out this guide of the best things to do in Chicago over Labor Day weekend.

Hit Up a Neighborhood Festival

Outdoor neighborhood festivals are a staple of Chicago summers. Labor Day weekend is a great time to check one out while the weather's still nice enough to enjoy being outside. From food to art fests, there's plenty to see, do, and eat.

1. West Loop Art Festival

Source: Star Events

Get your culture on at the fifth annual West Loop Art Festival on September 2nd and September 3rd. Take a stroll and enjoy over four blocks of amazing art, wine tastings, interactive art experiences, children's crafts, and live music.

Plus, the West Loop plays an important role in the labor movement. Did you know we have 8-hour workdays because of an event that took place there? What a fitting spot to spend Labor Day weekend! Now, it's a true foodie paradise with nods to its working-class roots amongst the many Michelin-starred restaurants. If you want to learn more, join Chicago Food & City Tours after the art fest on their Gateway to the West Loop food tour for a delicious inside look at this dynamic neighborhood.

2. African Festival of the Arts

Source: African International House USA, Inc.

The African Festival of the Arts returns to Washington Park for its 34th year September 1st through September 4th. Visitors will feel transported in this event that celebrates the cultures of the African Diaspora in a recreated African village. Listen to music, see movie screenings, attend book signings, eat traditional food, shop for African goods, and more at one of the largest neighborhood festivals in Chicago.

3. Taste of Polonia

Source: Taste of Polonia Chicago

America's largest Polish festival happens in Chicago's Jefferson Park over Labor Day weekend from September 1st to September 4th. Eat your fill of Polish favorites like pierogis, kielbasa, and potato pancakes. Then, if you're feeling inspired, take a cooking class or attend a tasting. Quench your thirst at the beer garden and get down to non-stop live music. Families can dance together at the Kids Stage and go on carnival rides. If you're feeling lucky, they even have a casino!

4. WingOut Chicago

Source: Green Curtain Events

Wild about wings? Head to Gallagher Way in Wrigleyville on September 2nd and September 3rd for a chicken wing extravaganza. Sample classic and creative chicken wings from over 13 different vendors while you listen to music and sip on beverages right in front of Wrigley Field.

Listen to Live Music

For many, Labor Day weekend in Chicago is synonymous with music festivals. This year's fests are sure to please, from jazz legends to electric dance music. Get a ticket and get ready to boogie!

5. Chicago Jazz Festival

Source: DCASE

The Chicago Jazz Festival returns to Millenium Park and the Chicago Cultural Center this year with a killer lineup of legendary jazz musicians. From August 31st to September 3rd, vibe out to music from icons such as Ron Carter and Foursight, Dianne Reeves, Makaya McCraven, and Juan de Marcos and the Afro-Cuban All Stars, to name a few. Did we mention it's free?

6. North Coast Music Festival

Source: North Coast Festival

If your idea of a relaxing three-day weekend involves waiting for the bass to drop, get tickets to North Coast Festival. Some of the biggest names in EDM all converge at SeatGeek Stadium in Bridgeview, IL from September 1st through September 3rd. Headliners include Marshmello, Zeds Dead, and Flume. There're six stages of house, techno, progressive, and trance music, so you'll have plenty to dance to this weekend.

7. ARC Music Festival

Source: EDMIdentity

Chicago is the birthplace of house music and ARC Music Festival is an all-out celebration of the genre. From September 1st through September 3rd, some of the best dance music artists put on epic shows at Union Park. Headliners include Fatboy Slim, Eric Prydz presents HOLO, John Summit, and Black Coffee.

Visit Navy Pier

Think of Navy Pier like Chicago's playground on the lake. Sounds like a great place to spend Labor Day weekend! From dazzling fireworks displays to family fun activities, head to the Pier for a great time. For an even more in-depth look at Navy Pier, check out this guide.

8. Summer Fireworks Saturday

Source: Navy Pier

Navy Pier's spectacular Saturday fireworks ends Labor Day weekend. That's right, this is your last weekend to watch the magic! Find a spot on the pier to take in the display, or better yet, book a fireworks dinner cruise for dinner and a show.

9. Pixar Putt

Source: Pixar Putt

Experience this mini golf pop-up through September 6th at Polk Bros Park on Navy Pier. With 18 holes inspired by Pixar's most beloved movies, like Toy Story, Finding Nemo, and Ratatouille, this course is sure to delight visitors of all ages. Want to leave the kids at home? Visit Thursdays-Sundays from 7-10pm for Pixar Putt After Dark, open only for those 18 and older. Illinois residents even get $3.50 tickets with proof of residency. Hole in one!

10. Offshore Rooftop

Source: Offshore

Brag to your friends that you dined at the largest rooftop deck in the country. Enjoy delicious California-inspired cuisine and beautiful views of Lake Michigan from this Chicago hotspot. Whether you go for Friday happy hour to kick off your weekend or Sunday brunch to recover from a night out, you're sure to have a fantastic time at Offshore Rooftop.

Get Active

Take advantage of late summer weather and get outside! Whether you're looking for a bike ride on Chicago's most iconic road or a leisurely stroll with food, there's plenty to do in Chicago to keep you moving and grooving!

11. Bike the Drive

Source: Anne Evans

For just one glorious day out of the year, the famous Lake Shore Drive is closed to all vehicular traffic for a giant 30-mile bike ride. On Sunday, September 3rd, grab your bike or rent one and join in the fun of Bike the Drive. There's 5 entry points along the route, so riders can make the ride as long or short as they want. The official start time is 6:30am, but riders can start any time before 10:30am. Plus, proceeds from Bike the Drive support the Active Transportation Alliance, a nonprofit organization that works to improve conditions for pedestrians and cyclists throughout Chicago.

12. Millennium Park Summer Workouts

Source: WTTW

Kickstart your weekend with a free pilates or yoga class at on the Great Lawn of Millennium Park. This Saturday, September 2nd is the last class of the season, so bring your yoga mat and get ready to stretch. Spanish guitarist Carlos Basile provides the soothing soundtrack to your workout. Plus, after your workout, you'll get a reward for a job well done! If you bring your workout mat to the Double Clutch Cafe below the Cloud Gate (aka The Bean), you'll get a complimentary mimosa with any entree off their special menu just for workout participants.

13. Wateriders Kayak Tours & Rental

chicago kayak tours

Source: Wateriders

See the city from the water on a kayak tour. Veteran tour operator Wateriders has been around since 1997 and has hosted more than 100,000 enthusiasts on its many tours. During the day, go on a History & Architecture Tour. And then at night, come back for an epic view of the Navy Pier fireworks, a Sunset Paddle, or Moonlight Paddle. Feeling spooky? Try their Ghosts & Gangsters Tour for a night of city lights and frights. 

Worried you’re not ready to take off in your own kayak? Wateriders offers an “on-land” lesson to everyone who books a tour, and all leaders are also experienced kayakers who will lend a helping hand to nervous tour participants who don’t quite have their sea legs.

14. Chicago Food & City Tours

Soure: Chicago Food & City Tours

Feed your belly and your brain on a walking food tour! Chicago Food & City Tours is a 2023 TripAdvisor Travelers' Choice winner, meaning they're in the top 10% of attractions worldwide. So that means that you're guaranteed to have a great time on one of their walking tours.

If you're new to the city, check out the Iconic Foods of Chicago Tour and sample the Chicago classics like deep dish pizza, Italian beef, Chicago hot dogs, Garrett Popcorn, and brownies. Architecture buffs will love the Buildings & Bites tour and foodies will feel right at home on the Gateway to the West Loop tour. More adventurous travelers will love the Chinatown Adventure food tour and the Street Foods of Pilsen Mexican food tour for vibrant and authentic cultural experiences.

Experience Movie Magic

Film buffs have plenty of fun options this Labor Day weekend in Chicago that take you outside of dark theaters and put you in the middle of the action. From outdoor cinema to immersive movie experiences, these events are sure to please even the most discerning of cinephiles.

15. Harry Potter Magic at Play

Source: Harry Potter™: Magic at Play

Grab your wizarding robes and head to the final weekend of Harry Potter™: Magic at Play at Water Tower Place. Feel like a true witch or wizard as you explore three floors of magic in this immersive experience. Journey to Hogwarts™, play Quidditch™, learn spells and potions, and more! If only there were a spell to make Labor Day weekend last longer!

16. Rooftop Cinema Club Fulton Market

Source: Rooftop Cinema Club

Movie under the stars anyone? Grab some popcorn and head to the Rooftop Cinema Club Fulton Market on the roof of the Emily Hotel in West Loop. This is no ordinary movie-watching experience: with your ticket, you'll receive a pair of state-of-the-art headphones, so you won't miss a line over the sounds of the city or the guy next to you eating popcorn too loudly. Choose from a comfy single deck chair or a love seat for a cozy date. Enjoy classic cinema snacks plus beer, wine, and cocktails.

Their Summerween series kicks off August 31st through September 3rd so you can enjoy spooky favorites like Jaws, Hocus Pocus, Get Out, and The Nightmare Before Christmas before Halloween kicks off in October. Scary not your thing? On Labor Day, catch showings of The Sandlot, Love & Basketball, and Pulp Fiction.

17. Malibu Barbie Cafe

Source: Bucketlisters

It's the summer of Barbie! If you want to feel like you're in the Barbie movie, head to the Malibu Barbie Cafe Chicago. You'll be transported to Barbie's Malibu Dream House where you'll dine on Barbie-inspired fare from Master Chef finalist Chef Becky Brown, like Paradise Pancakes and California Dreamin' Club Sandwiches. It's a full-on immersive experience filled with tons of great photo ops, like a life-size Barbie box, perfect for posing with your besties.

There's even a roller skating add-on experience for $1 where 100% of the proceeds go towards Girls Inc. Chicago, an organization that delivers life-changing programs and experiences that inspire girls to be strong, smart and bold enough to overcome challenges. Come on Barbie, let's go Barbie!

18. ChiTown Movies Drive-In

Source: ChiTown Movies

ChiTown Movies brings a taste of the 1950s to Pilsen with their drive-in movie theater. Pile the whole family (including the dog) into your car and grab a parking spot in front of the big screen. Order tasty treats like pizza, popcorn, tacos, and wings from ChiTown Grill and they'll bring your food right to your car!

Over Labor Day weekend catch showings of John Wick 4, The Notebook, Us, Guardians of the Galaxy 4, Nightmare on Elm Street, Super Mario Bros, and It: Volume 2. 

Catch a Ball Game

19. Chicago Cubs or Chicago White Sox

chicago wrigley field tours

Source: Wikipedia

Northsiders and Southsiders alike can cheer on their favorite teams in Chicago this Labor Day Weekend. The Chicago White Sox face off against the Detroit Tigers in three games on September 1st, 2nd, and 3rd. Enjoy post-game fireworks on the 1st and the first 20,000 fans get a free Los White Sox Soccer Jersey on the 2nd. On the 3rd, Star Wars fans can purchase a special ticket for Star Wars Day.

On Monday, September 4th, the Chicago Cubs go head-to-head against the San Fransisco Giants in a day game. Grab your mitt and head to the friendly confines!

20. Chicago Football Classic

Source; HBCU Gameday

The Chicago Football Classic (CFC) returns to Soldier Field after a three-year hiatus for its 25th anniversary. This year, the Central State Marauders and Mississippi Valley State Delta Devils go head-to-head on Saturday, September 2nd. Come by before 3pm kickoff for a HBCU (Historically Black Colleges & Universities) Battle of the High School Bands, tailgating, college and career fair and empowerment summit, vendor marketplace, and more.

The best part? Over $300,000 in scholarships have been awarded to 20 Chicagoland students attending HBCUs. The CFC is truly more than just a game.

Celebrate Labor Day

We couldn't create a guide to Labor Day weekend in Chicago without including a celebration of the holiday itself. Check out below for more information about Chicago's Labor Day Parade.

21. Chicago Labor Day Parade

Source: Chicago Tribune

Chicago's first Labor Day Parade took place in 1880, even before it was made a national holiday in 1884! The parade has moved many times over the years and was even resurrected in 2015 after it fell off in the 2000s. This is the first year that the route moves to the historic Pullman District on the South Side, a neighborhood with historic ties to the labor movement. In fact, the struggle inside Pullman's factory town gave rise to Labor Day! This year's parade starts at noon on Saturday, September 2nd and runs from 103rd to 108th Streets along Cottage Grove Ave.

Following the parade is Eddie Fest, named for Chicago labor activist Eddie Sadlowski. There'll be food, music, fireworks, and more honoring the workers and the great Chicago labor movement.

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