| Date | Event | Venue |
|---|---|---|
| 31 Aug 2025 | Labor Day Weekend Evening Lake Cruise on Sunday August 31st | Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location), Chicago |
| 28 Aug 2025 | Mecca Chicago Steppers Homecoming Labor Day Weekend | Hyatt Regency McCormick Place Chicago |
| 01 Sep 2025 | "The Lake House" (Labor Day) 91 | Summer Of George, Chicago |
| 31 Aug 2025 | LDW SUNDAY NIGHT - Afrobeats Amapiano & More Masada | To Be Announced, Chicago |
| 30 Aug 2025 | All White Attire RnB Vs Hip Hop Yacht Cruise (Labor Day WKD) Chicago | Anita Dee Yacht Charters, Chicago |
| 30 Aug 2025 | Labor Day Weekend Evening Lake Cruise on Saturday August 30th | Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location), Chicago |
| 01 Sep 2025 | Labor Day Cruise on Lake Michigan 21 Live DJ Full Bar | Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location), Chicago |
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!
Chicagoland’s biggest Labor Day Weekend Festival North Coast Music Festival 2024 returns to SeatGeek Stadium Campus! Art, Music, Food & Drinks spread across artificial turf soccer fields provide attendees with the best end-of-summer mud-free festival experience. Enjoy stunning art installations and six top-tier stages filled with dozens of talented artists, allowing you to make your North Coast experience truly your own.
Bringing the global scene to the birthplace of house music. The 3rd 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 7th 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.
For all Softball players gather at the picturesque Chicago Lakefront Fields on September 2, the 2024 Labor Day Softball Tournament will occur. All teams are guaranteed at least three games in the coed 12-inch, men's 12-inch, coed 16-inch, and men's 16-inch divisions. This is a one-day competition. It's the ideal way to enjoy some friendly rivalry and companionship on Labor Day.
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