CHICAGO LABOR DAY WEEKEND MUST-DO'S—FESTIVALS, CRUISES AND MORE!

JUL 2024
04
CHICAGO LABOR DAY WEEKEND MUST-DO'S—FESTIVALS, CRUISES AND MORE!

End summer with Chicago’s best Labor Day events and festivities.


Planning for Labor Day Weekend in Chicago?

It's your final chance to soak in the sunshine and warm weather before summer ends.

Also perfect for that epic family adventure before school begins.

Enjoy the iconic parade, visit the Pullman Historic District, join the festivals, or relax at the beach—there’s plenty to do.

Get ready to make the most of the long September weekend!


Pro Tip: Bookmark this page now—your ultimate Chicago Labor Day resource gets updated annually!

Watch the parade

Head to the historic Pullman District for the Chicago Labor Day Parade.

Expect plenty of Insta-worthy moments from the marching bands, colorful floats, and enthusiastic participants.


And then hang around for Eddie Fest, especially if you’re a parent. This family-friendly event includes live music, bounce houses, outdoor exhibits, and food trucks.


Website: Visit the Parade website


Date & Time: Saturday, August 31st, 2024. Begins at noon.


Location: Plan your route on Google Maps (Pullman District)

Visit historical sites and monuments

A bastion of organized labor, Chicago has several Labor Day sites and monuments. History buff or otherwise, a visit should be fascinating.

Pullman Historic District

The Pullman District was America's first planned industrial community.

It was built in 1865 for the workers of the Pullman Palace Car Company.

Join the First Sunday Walking Tour to marvel at the charming houses and streets, and catch stories of engineering excellence and the early labor movement in Chicago.

The Haymarket Memorial and The Haymarket Martyr’s Monument

On May 4th, 1886, several policemen and civilians were killed at a labor protest at Haymarket Square.

Eight protesters were prosecuted…some say unfairly.

The Haymarket Memorial and the Haymarket Martyrs' Monument honor the day's tragic events.

See the Navy Pier fireworks

Enjoy the Navy Pier summer fireworks grand finale during Labor Day Weekend!

You should also hop on the Centennial Wheel and catch a ride on the Light Tower and Carousel

Afterward, unwind with a drink at the Beer Garden.


Website: Visit the Navy Pier website


Date & Time: Saturday, August 31st, 2024. Begins at 10 PM.


Location: Plan your route on Google Maps

Visit Labor Day festivals

Labor Day in the Windy City is incomplete without music festivals and neighborhood events. Whether you're into jazz or electronic music, or just want to experience local culture, there’ll be something for you.

Labor Day music festivals in Chicago

Neighborhood Labor Day events

  • African Festival of the Arts: Experience African cultures in a recreated African village at this end-of-summer festival in Washington Park. Enjoy live music, dancing, food stalls, and vendors.

  • West Loop Art Fest: Check out different paintings, from interactive art to children’s crafts, at Fulton Market. Excellently paired with wine tastings and live music.

  • Sky Blue Music and Culture Festival: Enjoy music, art, and community presentations in the Woodlawn neighborhood. 2024 will be the second edition of this fest.

Go for a cruise

Embark on a breathtaking boat cruise along Chicago's vibrant waterfronts. Choose from these top options for Labor Day - 


Catch a game

Sports fans are in for a treat this Labor Day. 

The White Sox are playing the Mets (Aug 30th to Sep 1st), the Cubs face the Pirates (Sep 2nd), and Chicago Sky tries to best Indiana Fever (Aug 30th).

If you're looking for reasons to visit Chicago over the Labor Day Weekend, this might be it!

Go for a walk

Explore Chicago while stretching the legs and catching fresh air during Labor Day Weekend. Take your pick from leisurely waterfront strolls to scenic walks through a park and even runs.

The Chicago Riverwalk

The Riverwalk is the ultimate urban escape with fantastic food, eye-catching public art, and breathtaking views. 

Open throughout the weekend, it’s ideal for marveling at Windy City architecture and enjoying a drink at a stunning waterfront. 

Make a reservation at one of its many restaurants and bars ahead of Labor Day.

Maggie Daley Park

Maggie Daley Park features winding paths, beautiful gardens, and attractions like the Skating Ribbon, Picnic Groves, and Mini Golf. 

Whether with friends & family or solo, you’ll find plenty of spots to relax in and explore.

CARA Runs

Want to go a little more hardcore than just walking? 

Check what CARA (Chicago Area Runners’ Association) programs are available over the Labor Weekend.

Dine out

Is there ever a bad time to dine out in Chicago? 

Mark the end of summer during Labor Day with a whirlwind of outdoor dining, brewery visits, and food festivals.

Hit up some outdoor restaurants

Enjoy the last days of patio dining weather at some of Chicago's top outdoor restaurants from the West Loop to the riverfront.


Enjoy yourself at rooftop bars and restaurants

  • Cindy’s Rooftop: Enjoy seasonal dishes and craft cocktails against panoramic views of Millennium Park and Lake Michigan.

  • Offshore Rooftop: Located at Navy Pier, this is the world's largest rooftop venue. With stunning lake views and a creative menu, it's perfect for a Labor Day get-together.

Try Chicago’s breweries

Did you know Chicago is one of the nation’s best craft beer cities? 

Check out brewing hot spots like Malt Row in Ravenswood or the Chicago Brewing District on the West Side. 

Whether you're an aficionado or just looking for a cold one, these breweries are a perfect Labor Day Weekend getaway.

Taste of Polonia

Celebrate Chicago's rich Polish heritage at the Taste of Polonia festival in Jefferson Park.

Running from Friday, August 30th, to Monday, September 2nd, it features traditional Polish food & beer, music & dance, and cultural exhibits. 

Got kids? Take them along for bounce inflatables, climbing walls, face painting, and clowns.

Chi Food Truck Fest

Like food truck fare?

Then you should definitely visit the Chi Food Truck Fest at Daley Plaza.

It’s on Friday, August 30th, and should whet your appetite for Labor Weekend! 

Hit the beach!

Chicago beach season ends on Labor Day. So this is your final chance to quench beach fever till Memorial Day next year!


  • North Avenue Beach: Check out the stunning skyline and bustling beach house with a rooftop bar at this Lincoln Park beach.

  • Oak Street Beach: Go swimming and sunbathing at this beach near the Gold Coast.

  • Montrose Beach: If you’re a pet owner, this pet-friendly shore with scenic dunes should be your Labor Day destination.


Pro Tip: Check beach conditions before making plans. You may find them a little crowded, as many others will also be looking to enjoy a final day of sand and surf before the beaches close.

Other things to try on Labor Day in Chicago

Visit museums

  • Field Museum: Discover historical wonders, including Sue the T. rex and ancient Egyptian artifacts.

  • Griffin Museum of Science and Industry: Engage with interactive exhibits like the U-505 submarine and the science of storms.

  • Art Institute: Admire masterpieces such as Grant Wood's "American Gothic" and Georges Seurat's "A Sunday on La Grande Jatte."

  • Museum of Ice Cream: Indulge in sweet treats while exploring colorful, Instagrammable installations.

  • Museum of Illusions: Challenge your perception with mind-bending optical illusions and immersive rooms.

Try escape rooms

  • Fox in a Box (That’s Us): Solve thrilling puzzles and escape scenarios ranging from a serial killer thriller to a Cold War bunker.

  • Escape Artistry: Experience Chicago-themed escape rooms, including a runaway El train and a steampunk time machine.

  • PanIQ Escape Room Chicago: Immerse in themes like a medieval castle, a voodoo shop, and a secret military bunker.

Stroll through and shop at farmers markets

Enjoy community vibes while shopping fresh & local produce at Chicago's farmers markets during Labor Day Weekend. 

Visit the Green City Market in Lincoln Park for organic produce, artisanal cheeses, and freshly baked goods. 

Take your pick from vendors selling everything from fresh flowers to locally sourced honey at the Logan Square Farmers Market

And don’t miss the Daley Plaza Market, where you can find a wide range of fruits, vegetables, and homemade jams.

Check out the street art

Explore Chicago’s street art scene with murals and installations. Drop by the Wabash Art Corridor, where you can admire large-scale works by local and international artists.

Labor Day attractions in Chicago suburbs

  • Septemberfest in Schaumburg: Enjoy music, craft beer & wine, bingo, fireworks, and more at Schaumburg’s end-of-summer carnival.

  • North Coast Music Festival: Dance the weekend away with top EDM and hip-hop acts. Since 2021, the festival has been held at the SeatGeek Stadium in Bridgeview.

  • Naperville Last Fling: Celebrate the end of summer with family-friendly activities, live music, and a colorful parade.

  • Frankfort Fall Festival: Explore charming artisan crafts, local food vendors, and live entertainment in a quaint downtown setting.

Hotels for tourists to stay during Labor Day Weekend in Chicago

  • The Peninsula Chicago: Experience unmatched elegance and world-class service with a rooftop spa and exquisite dining.

  • Palmer House Hilton: Historic charm blended with modern amenities at this iconic hotel in downtown Chicago.

  • The Kimpton Gray Hotel: This stylish hotel offers contemporary comfort with chic rooms, a rooftop bar, and a convenient location.

  • Freehand Chicago: A trendy and affordable option in River North, offering shared and private rooms, a bar, and easy access to public transportation and local hotspots.

Resources for planning your Labor Day outing in Chicago

  • Choose Chicago: Your go-to guide for the latest on events, dining, and accommodations in the city.

  • City of Chicago website: Official updates on city-wide celebrations, including parades and public events.

  • OEMC App: Stay informed with real-time emergency alerts, weather advisories, and city-wide updates.

  • Chicago Park District: Find the best parks for picnics, fireworks viewing, and outdoor activities.

  • Divvy: Rent a bike to explore the city’s lakefront and neighborhoods at your own pace. Website.

  • SpotHero: Book parking in advance and avoid the hassle of finding a spot during busy events.

  • Ventra App: Load your “L” card and plan your public transit routes easily.

  • The CTA Website: Get real-time updates on buses and trains, ensuring you’re never late to the festivities.

  • Chicago CityPASS and Go Chicago Pass: Visit multiple attractions with one ticket.

Frequently asked questions

Is Labor Day a good time to visit Chicago?

Absolutely! Labor Day is one of the best times to visit Chicago. 

The weather is still warm, and there's a festive atmosphere with plenty of events, from parades and music festivals to cruises and outdoor dining. 

Plus, it's your last chance to enjoy the beach before summer ends!

What kind of weather should I expect on Labor Day?

Expect warm and pleasant weather during Labor Day in Chicago. 

Temperatures are perfect for outdoor activities like festivals, cruises, and beach outings.

Pack light clothing such as shorts, t-shirts, and comfortable shoes, and don't forget a light jacket or sweater for the cooler evenings.

And do remember to check the forecast before visiting!

Is Chicago busy on Labor Day?

Yes, Chicago is bustling on Labor Day. 

Expect lively crowds at popular spots like the Navy Pier, beaches, and major festivals. 

Planning ahead and making reservations can help you navigate the busy weekend smoothly.

Is the Chicago Jazz Festival free?

Yes, the Chicago Jazz Festival is free!

Ready for an epic Labor Day Weekend in Chicago?

From parades to cruises, Chicago’s Labor Day Weekend has something for everyone. 

So pack your bags, make your plans, and get ready to experience the Windy City like never before. 

Enjoy the last rays of summer and create unforgettable memories this Labor Day!



  BLOGS
CHICAGO LABOR DAY WEEKEND MUST-DO'S—FESTIVALS, CRUISES AND MORE!

End summer with Chicago’s best Labor Day events and festivities.


Planning for Labor Day Weekend in Chicago?

It's your final chance to soak in the sunshine and warm weather before summer ends.

Also perfect for that epic family adventure before school begins.

Enjoy the iconic parade, visit the Pullman Historic District, join the festivals, or relax at the beach—there’s plenty to do.

Get ready to make the most of the long September weekend!


Pro Tip: Bookmark this page now—your ultimate Chicago Labor Day resource gets updated annually!

Watch the parade

Head to the historic Pullman District for the Chicago Labor Day Parade.

Expect plenty of Insta-worthy moments from the marching bands, colorful floats, and enthusiastic participants.


And then hang around for Eddie Fest, especially if you’re a parent. This family-friendly event includes live music, bounce houses, outdoor exhibits, and food trucks.


Website: Visit the Parade website


Date & Time: Saturday, August 31st, 2024. Begins at noon.


Location: Plan your route on Google Maps (Pullman District)

Visit historical sites and monuments

A bastion of organized labor, Chicago has several Labor Day sites and monuments. History buff or otherwise, a visit should be fascinating.

Pullman Historic District

The Pullman District was America's first planned industrial community.

It was built in 1865 for the workers of the Pullman Palace Car Company.

Join the First Sunday Walking Tour to marvel at the charming houses and streets, and catch stories of engineering excellence and the early labor movement in Chicago.

The Haymarket Memorial and The Haymarket Martyr’s Monument

On May 4th, 1886, several policemen and civilians were killed at a labor protest at Haymarket Square.

Eight protesters were prosecuted…some say unfairly.

The Haymarket Memorial and the Haymarket Martyrs' Monument honor the day's tragic events.

See the Navy Pier fireworks

Enjoy the Navy Pier summer fireworks grand finale during Labor Day Weekend!

You should also hop on the Centennial Wheel and catch a ride on the Light Tower and Carousel

Afterward, unwind with a drink at the Beer Garden.


Website: Visit the Navy Pier website


Date & Time: Saturday, August 31st, 2024. Begins at 10 PM.


Location: Plan your route on Google Maps

Visit Labor Day festivals

Labor Day in the Windy City is incomplete without music festivals and neighborhood events. Whether you're into jazz or electronic music, or just want to experience local culture, there’ll be something for you.

Labor Day music festivals in Chicago

Neighborhood Labor Day events

  • African Festival of the Arts: Experience African cultures in a recreated African village at this end-of-summer festival in Washington Park. Enjoy live music, dancing, food stalls, and vendors.

  • West Loop Art Fest: Check out different paintings, from interactive art to children’s crafts, at Fulton Market. Excellently paired with wine tastings and live music.

  • Sky Blue Music and Culture Festival: Enjoy music, art, and community presentations in the Woodlawn neighborhood. 2024 will be the second edition of this fest.

Go for a cruise

Embark on a breathtaking boat cruise along Chicago's vibrant waterfronts. Choose from these top options for Labor Day - 


Catch a game

Sports fans are in for a treat this Labor Day. 

The White Sox are playing the Mets (Aug 30th to Sep 1st), the Cubs face the Pirates (Sep 2nd), and Chicago Sky tries to best Indiana Fever (Aug 30th).

If you're looking for reasons to visit Chicago over the Labor Day Weekend, this might be it!

Go for a walk

Explore Chicago while stretching the legs and catching fresh air during Labor Day Weekend. Take your pick from leisurely waterfront strolls to scenic walks through a park and even runs.

The Chicago Riverwalk

The Riverwalk is the ultimate urban escape with fantastic food, eye-catching public art, and breathtaking views. 

Open throughout the weekend, it’s ideal for marveling at Windy City architecture and enjoying a drink at a stunning waterfront. 

Make a reservation at one of its many restaurants and bars ahead of Labor Day.

Maggie Daley Park

Maggie Daley Park features winding paths, beautiful gardens, and attractions like the Skating Ribbon, Picnic Groves, and Mini Golf. 

Whether with friends & family or solo, you’ll find plenty of spots to relax in and explore.

CARA Runs

Want to go a little more hardcore than just walking? 

Check what CARA (Chicago Area Runners’ Association) programs are available over the Labor Weekend.

Dine out

Is there ever a bad time to dine out in Chicago? 

Mark the end of summer during Labor Day with a whirlwind of outdoor dining, brewery visits, and food festivals.

Hit up some outdoor restaurants

Enjoy the last days of patio dining weather at some of Chicago's top outdoor restaurants from the West Loop to the riverfront.


Enjoy yourself at rooftop bars and restaurants

  • Cindy’s Rooftop: Enjoy seasonal dishes and craft cocktails against panoramic views of Millennium Park and Lake Michigan.

  • Offshore Rooftop: Located at Navy Pier, this is the world's largest rooftop venue. With stunning lake views and a creative menu, it's perfect for a Labor Day get-together.

Try Chicago’s breweries

Did you know Chicago is one of the nation’s best craft beer cities? 

Check out brewing hot spots like Malt Row in Ravenswood or the Chicago Brewing District on the West Side. 

Whether you're an aficionado or just looking for a cold one, these breweries are a perfect Labor Day Weekend getaway.

Taste of Polonia

Celebrate Chicago's rich Polish heritage at the Taste of Polonia festival in Jefferson Park.

Running from Friday, August 30th, to Monday, September 2nd, it features traditional Polish food & beer, music & dance, and cultural exhibits. 

Got kids? Take them along for bounce inflatables, climbing walls, face painting, and clowns.

Chi Food Truck Fest

Like food truck fare?

Then you should definitely visit the Chi Food Truck Fest at Daley Plaza.

It’s on Friday, August 30th, and should whet your appetite for Labor Weekend! 

Hit the beach!

Chicago beach season ends on Labor Day. So this is your final chance to quench beach fever till Memorial Day next year!


  • North Avenue Beach: Check out the stunning skyline and bustling beach house with a rooftop bar at this Lincoln Park beach.

  • Oak Street Beach: Go swimming and sunbathing at this beach near the Gold Coast.

  • Montrose Beach: If you’re a pet owner, this pet-friendly shore with scenic dunes should be your Labor Day destination.


Pro Tip: Check beach conditions before making plans. You may find them a little crowded, as many others will also be looking to enjoy a final day of sand and surf before the beaches close.

Other things to try on Labor Day in Chicago

Visit museums

  • Field Museum: Discover historical wonders, including Sue the T. rex and ancient Egyptian artifacts.

  • Griffin Museum of Science and Industry: Engage with interactive exhibits like the U-505 submarine and the science of storms.

  • Art Institute: Admire masterpieces such as Grant Wood's "American Gothic" and Georges Seurat's "A Sunday on La Grande Jatte."

  • Museum of Ice Cream: Indulge in sweet treats while exploring colorful, Instagrammable installations.

  • Museum of Illusions: Challenge your perception with mind-bending optical illusions and immersive rooms.

Try escape rooms

  • Fox in a Box (That’s Us): Solve thrilling puzzles and escape scenarios ranging from a serial killer thriller to a Cold War bunker.

  • Escape Artistry: Experience Chicago-themed escape rooms, including a runaway El train and a steampunk time machine.

  • PanIQ Escape Room Chicago: Immerse in themes like a medieval castle, a voodoo shop, and a secret military bunker.

Stroll through and shop at farmers markets

Enjoy community vibes while shopping fresh & local produce at Chicago's farmers markets during Labor Day Weekend. 

Visit the Green City Market in Lincoln Park for organic produce, artisanal cheeses, and freshly baked goods. 

Take your pick from vendors selling everything from fresh flowers to locally sourced honey at the Logan Square Farmers Market

And don’t miss the Daley Plaza Market, where you can find a wide range of fruits, vegetables, and homemade jams.

Check out the street art

Explore Chicago’s street art scene with murals and installations. Drop by the Wabash Art Corridor, where you can admire large-scale works by local and international artists.

Labor Day attractions in Chicago suburbs

  • Septemberfest in Schaumburg: Enjoy music, craft beer & wine, bingo, fireworks, and more at Schaumburg’s end-of-summer carnival.

  • North Coast Music Festival: Dance the weekend away with top EDM and hip-hop acts. Since 2021, the festival has been held at the SeatGeek Stadium in Bridgeview.

  • Naperville Last Fling: Celebrate the end of summer with family-friendly activities, live music, and a colorful parade.

  • Frankfort Fall Festival: Explore charming artisan crafts, local food vendors, and live entertainment in a quaint downtown setting.

Hotels for tourists to stay during Labor Day Weekend in Chicago

  • The Peninsula Chicago: Experience unmatched elegance and world-class service with a rooftop spa and exquisite dining.

  • Palmer House Hilton: Historic charm blended with modern amenities at this iconic hotel in downtown Chicago.

  • The Kimpton Gray Hotel: This stylish hotel offers contemporary comfort with chic rooms, a rooftop bar, and a convenient location.

  • Freehand Chicago: A trendy and affordable option in River North, offering shared and private rooms, a bar, and easy access to public transportation and local hotspots.

Resources for planning your Labor Day outing in Chicago

  • Choose Chicago: Your go-to guide for the latest on events, dining, and accommodations in the city.

  • City of Chicago website: Official updates on city-wide celebrations, including parades and public events.

  • OEMC App: Stay informed with real-time emergency alerts, weather advisories, and city-wide updates.

  • Chicago Park District: Find the best parks for picnics, fireworks viewing, and outdoor activities.

  • Divvy: Rent a bike to explore the city’s lakefront and neighborhoods at your own pace. Website.

  • SpotHero: Book parking in advance and avoid the hassle of finding a spot during busy events.

  • Ventra App: Load your “L” card and plan your public transit routes easily.

  • The CTA Website: Get real-time updates on buses and trains, ensuring you’re never late to the festivities.

  • Chicago CityPASS and Go Chicago Pass: Visit multiple attractions with one ticket.

Frequently asked questions

Is Labor Day a good time to visit Chicago?

Absolutely! Labor Day is one of the best times to visit Chicago. 

The weather is still warm, and there's a festive atmosphere with plenty of events, from parades and music festivals to cruises and outdoor dining. 

Plus, it's your last chance to enjoy the beach before summer ends!

What kind of weather should I expect on Labor Day?

Expect warm and pleasant weather during Labor Day in Chicago. 

Temperatures are perfect for outdoor activities like festivals, cruises, and beach outings.

Pack light clothing such as shorts, t-shirts, and comfortable shoes, and don't forget a light jacket or sweater for the cooler evenings.

And do remember to check the forecast before visiting!

Is Chicago busy on Labor Day?

Yes, Chicago is bustling on Labor Day. 

Expect lively crowds at popular spots like the Navy Pier, beaches, and major festivals. 

Planning ahead and making reservations can help you navigate the busy weekend smoothly.

Is the Chicago Jazz Festival free?

Yes, the Chicago Jazz Festival is free!

Ready for an epic Labor Day Weekend in Chicago?

From parades to cruises, Chicago’s Labor Day Weekend has something for everyone. 

So pack your bags, make your plans, and get ready to experience the Windy City like never before. 

Enjoy the last rays of summer and create unforgettable memories this Labor Day!



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