As summer gently gives way to the vibrant colors of fall, Chicago comes alive with an irresistible blend of energy, culture, and festivities. This Labor Day weekend in Chicago is poised to dazzle both locals and visitors with a captivating array of live music experiences and exciting activities. Whether you’re a music enthusiast, a foodie craving diverse flavors, or simply someone searching for memorable adventures, Chicago has something special in store for you.
In this guide, we’ll take you on a journey through the heart of Chicago’s entertainment scene, unveiling the hottest live music venues that will set your holiday in Chicago this weekend to its own rhythm. Celebrate the end of the season with scenic boat cruises, dinner on a patio, music under the stars (including the iconic Chicago Jazz Festival), exhilarating live sports, cocktails at the beach, and so much more.
Visit some Live Music Festival
Experiencing Labor Day in Chicago wouldn’t be complete without immersing yourself in the city’s traditional yearly music festivals. This year, the extended weekend boasts a captivating lineup of events. Attendees can enjoy performances by renowned jazz artists at no cost in Millennium Park, groove to the beats at a house music festival, and engage in various other musical festivities.
- Chicago Jazz Festival: The oldest of Chicago’s free lakefront music festivals boasts an incredibly diverse lineup in the heart of the loop.
- ARC Music Festival: This immersive fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.
- North Coast Music Festival: This annual Labor Day weekend music festival includes electronic music, hip hop, and rock acts, plus art installations and food vendors.
Attend a Neighborhood Festival
Summer may be winding down, but the festival season is still going strong. These popular summer festivals in Chicago celebrate the city’s diverse food, music, and arts scenes.
- 34th Annual African Festival of the Arts: This culturally immersive event recreates an African village in Washington Park, with live music, yoga, dancing, vendors, and culinary delights.
- Chicago Wing Festival: Sample a variety of award-winning wings and sauces in the heart of Wrigleyville, then vote for your favorites.
- Taste of Polonia Festival: Celebrate Chicago’s Polish heritage with live music, a casino, a beer garden, kids area, and of course, endless Polish food and beer.
- The Great American Lobster Fest: Enjoy live lobster flown in fresh from the cold waters of the East Coast (courtesy of Lobster Gram), live music performances, family-friendly games & activities, unique craft shopping, and cold beverages.
Take a Boat Cruise
Chicago’s beautiful boat tours set sail along one of the city’s two waterfronts. Choose from exciting speedboat excursions, memorable dinner cruises, tiki-themed party boats, sunset and fireworks cruises and more.
- Labor Day Sunday Funday Booze Cruise: Make the most of your Labor Day weekend with this booze cruise. Sail along Lake Michigan while enjoying drinks, music, and good company.
- Swiftie Booze Cruise Chicago: Calling all Taylor Swift fans! This cruise is tailor-made for Swifties. Enjoy a cruise dedicated to the music and vibe of Taylor Swift.
- Bollywood Boat Party & Fireworks Cruise: Celebrate Bollywood culture with music, dancing, and a fireworks display. Enjoy the energetic beats, colorful attire, and a unique blend of Indian culture while cruising along the waters of Chicago.
- The Lake House Sunset Cruise: Bid farewell to summer with a picturesque Labor Day Sunset Cruise on the lake. As the sun sets, soak in the breathtaking views, capturing the beauty of the transition from day to night.
- The Pilsen Cruise Latin Beats w/Fireworks Boat Party: Conclude the summer season with a bang at the Pilsen Cruise Latin Beats Finale. Dance to Latin rhythms, enjoy fiery performances and witness a spectacular fireworks display.
Bike down Lake Shore Drive
Get ready to pedal your way through the heart of the Windy City as the highly anticipated 2023 Bike the Drive returns for another exhilarating edition. Hosted by the Active Transportation Alliance, this iconic event invites cyclists of all ages and skill levels to experience the stunning views and car-free streets along Chicago’s beautiful Lake Shore Drive on Sep 03 2023 at 06:30 am.
Remember to check the event schedules and ticket availability in advance. So get your friends and family hyped and have a great time enjoying some fantastic events in Chicago.
