Labor Day unofficially marks the end of summer, and as fall sets in, we’re all set to savor the last few moments of the Chicago sun this Labor Day weekend, with cruises, music, and of course, cocktails. 

Labor Day at Navy Pier 

Fireworks at the Navy Pier, source: website 

The Beer Garden at the Navy Pier hosts free live music entertainment over three days of the Labor Day weekend. Besides this, Labor Day Weekend is your last chance to enjoy the summer fireworks at the Navy Pier. The pier also has a large Ferris wheel and many attractions for all ages during the day. At night, the colorful display is launched from the center of Lake Michigan. The fireworks take place on Saturday at 10:15 pm. Downtown rooftop bars are another great viewing spot. Alternatively, you can take a Fireworks Cruise on the lake for the most romantic experience.

Where - 600 E. Grand Avenue, Chicago, IL 60611

Buy Tickets here.

Chicago Jazz Festival

Live Jazz performance at Millennium Park, source: Facebook

Known for its artistic creativity, the Chicago Jazz Festival is a favorite Labor Day Weekend tradition. This incredible event draws outstanding musicians and celebrates jazz music with live performances. The celebration of jazz and creativity takes place at Millennium Park pavilions and the Chicago Cultural Center. The festival educates and encourages jazz audiences of all ages and showcases emerging jazz talent. Over the years, the event has hosted Ella Fitzgerald, Miles Davis, BB King, and many others.

Where - Millennium Park, 201 E Randolph St Chicago, IL 60601

Chicago Labor Day Weekend Pier Pressure White Party Cruise

Spirit of Chicago yacht, source: website 

Pier Pressure has organized one of the biggest yacht parties on Lake Michigan this Labor Day weekend. Sail through the Spirit of Chicago Yacht and enjoy the ultimate dance party. Here’s what to expect:

• An all-star line-up of Chicago's top DJs.
• Exclusive VIP area with a special view of the dance floor.
• Most gorgeous views of Chicago Skyline.

No alcohol, open containers, or outside food is permitted. No illegal drugs or controlled substances, including prescription drugs and marijuana, will be tolerated at the event.

Check-in - 10:30 pm
VIP Boarding - 11 pm
Cruise time - 12 am - 2 am

Where - Spirit of Chicago Yacht, 600 E Grand Ave, Chicago, IL 60611

Buy tickets here.

Weekend Cocktail Cruise

Source: website

Celebrate Labor Day on the water with the Chicago skyline and some delicious cocktails. There will be a full bar with cocktails available for purchase. You can not bring outside food at the party and there will be no food available. On the bright side, the different levels on the yacht are going to be blasting different genres of music, so groove to whatever floats your boat. 

21+ to board

Boarding time: 6:45 pm - 7:20 pm
Departure time: 7:30 pm
Return time: 10:00 pm

Where - Anita Dee II Yacht, DuSable Harbor, 200 N Breakwater Access, Chicago, IL 60601

Buy tickets here.

Labor Day Brunch

Interior of Cafe Ba-Ba-Reeba, source: Facebook

Take your time off and book a trip to Cafe Ba-Ba-Reeba for a sumptuous Labor Day Brunch. Cafe Ba-Ba-Reeba is Chicago’s original tapas bar, serving authentic Spanish cuisine since 1985. The menu is designed to share, featuring tapas, pintxos (bite-sized tapas), and the classic Valencian rice dish, paella. For brunch, you can try from their favorites like the Jamón Serrano Benedict with poached eggs. Pair the meal with sangria, craft cocktails, Spanish wine, or any local beers in their lively Lincoln Park restaurant. If you’d rather just swing by for a drink, don’t forget they also have a killer happy hour rolling.

Hours - 10 am - 9 pm

Where - 2024 N. Halsted St., Chicago, IL 60614

Header image, source: Chicago Jazz Festival