Anybody who’s been in Chicago on Labor Day Weekend knows it’s where you’ll find the best parties, concerts, sale shopping, sporting events, BBQ, and all-around fun – in one place – anywhere! And this year’s Labor Day Weekend in Chicago will be one of the most amazing ever! In addition to the last long weekend and the end of Summer, the time of the year is finally a bit cooler in Chicago, which means that the best parties are outside!
Chicago is a perfect spot to unwind during the long Labor Day Weekend. and If you’re among the thousands of people making plans for Labor Day weekend in Chicago, you’ll find no shortage of things to do while you’re here. To help you narrow down your options, we compiled this list of exciting things happening in Chicago over the long weekend.
A four-day into African culture & heritage immersive experience with 300 vendors, live African Diaspora music & family entertainment at the Annual African Festival of Arts . The nation’s largest Labor Day Weekend celebration of Black global cultures attracts over 75,000 culture enthusiasts to Chicago, Illinois’ southside museum district in Washington Park. This traditional end-of-summer, culturally immersive, and interactive event brings the art, sights, tastes, sounds, rhythms, and spirit of African Diaspora cultures to Chicago - in a replicated African village with over 300 vendors!
Join us for the All White Attire RnB vs Hip Hop Yacht Cruise on Saturday, 30th August 2025, from 1:30 pm to 5:00 pm aboard the Anita Dee #2 yacht at DuSable Harbor, 200 Breakwater Access, Chicago. Enjoy 3 levels of music with Chicago’s hottest DJs spinning Hip Hop, RnB, Top 40, and more. The event features indoor heated dance floors, a skydeck, stunning views of the Chicago skyline, and a fully stocked cash bar. It's a 21+ event, with VIP table reservations and food available for purchase. Boarding starts at 12:45 pm, and the yacht sails at 1:30 pm.
Bringing the global scene to the birthplace of house music. The 4th annual ARC Music Festival is scheduled to take over Union Park during Labor Day weekend, celebrating Chicago's house music roots and welcoming an international lineup of dance music artists. Taking place across three days, the fest features acts like Swedish DJs Eric Prydz and Adam Beyer, plus British pioneer Fatboy Slim. Additional Chicago performers include local house music legends Derrick Carter and DJ Lady D.
Chicago's Jazz Festival puts up a swinging Labor Day celebration! This event, which takes place at the storied Jazz Showcase, is a must-attend for jazz lovers. This 8th Annual Labor Day Jazz Festival takes in the mastery of five magnificent hours of performances by renowned musicians, from up-and-coming talents to seasoned veterans. In the cozy Jazz Showcase atmosphere, celebrate the city's musical history and unwind after a busy weekend.
Join us for the Sunday Funday Sunset Cruise on Sunday, 31st August 2025, from 7:30 pm to 10:30 pm at Chicago Lakefront Cruises, 900 South Wells Street. Cruise the Chicago River and Lake Michigan with live music by DJ Tecknique, spinning Top 40, EDM, and Hip-Hop. Enjoy stunning skyline views, a lively party atmosphere, and bar service on board. This 21+ event is the perfect way to cap off your Labor Day weekend in style!
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