Chicago Labor Day Events

Saturday Night Labor Day Fireworks Booze Cruise!

Chicago Lakefront Cruises 30 Aug 2025

All White Attire RnB Vs Hip Hop Yacht Cruise (Labor Day WKD) Chicago

Anita Dee Yacht Charters 30 Aug 2025

8th Annual Labor Day Jazz Festival 2025

Millennium Park 28 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) 30 Aug 2025

Bachata Fest with Bachata Legends Danny D Xtreme & Bachata Heighz!

Alhambra Palace Restaurant 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) 31 Aug 2025

Baila Habibi All White Yacht Party

Anita Dee Yacht Charters 29 Aug 2025

35TH ANNUAL AFRICAN FESTIVAL OF THE ARTS

Washington Park 30 Aug 2025

Mecca Chicago Steppers Homecoming Labor Day Weekend

Hyatt Regency McCormick Place Chicago 28 Aug 2025

Labor Day Sunday Funday Sunset Cruise!

Summer Of George 31 Aug 2025

Howl at the Moon Chicago's Pop Weekend

Howl at the Moon Chicago 29 Aug 2025

Labor Day Weekend All White Yacht Party | Anita Dee Yacht | Chicago

Navy Pier Marina 30 Aug 2025

Labor Day Weekend- SSSSHH

Park Tavern 29 Aug 2025

For the Love of R&B and Reggae @ The Reading Room

Reading Room 31 Aug 2025

Standup Seminary // MONDAYS // August 18-Sept 30

The Lincoln Lodge 18 Aug 2025

Fem Com // MONDAYS // August 18-Sept 29

The Lincoln Lodge 18 Aug 2025

DD3 - LIVE at The Dock at Montrose Beach

The Dock at Montrose Beach 28 Aug 2025

Afrobeats FRIDAYZ - Labor Day Weekend Edition

Masada 29 Aug 2025

RATIO: Chicago Edition

NEVER HAVE I EVER 29 Aug 2025

"The Lake House" (Labor Day) 9/1

Summer Of George 1 Sep 2025

Afrobeats SATURDAYZ - Labor Day Weekend Edition

Masada 30 Aug 2025

Kinzie Industrial Walking Tour

CTA Ashland Station (Pink and Green Line) 31 Aug 2025

LDW SUNDAY NIGHT - Afrobeats, Amapiano & More @ Masada

To Be Announced 31 Aug 2025

Labor Day Weekend Drag Brunch

Lark 30 Aug 2025

LAVISH THE ULTIMATE VIRGO CELEBRATION!!!! WHITE & GOLD AFFAIR

Juliana Restaurant 30 Aug 2025

Newport Theater presents: SLAYAWAY CAMP

The Newport Theater 30 Aug 2025

PRETTY THINGS @ CERISE ROOFTOP

Cerise Rooftop 1 Sep 2025

Fulton Market Walking Tour

Morgan Station 30 Aug 2025

Fem Com presents: The Punch Up // MONDAYS // Aug 18-Sept 29

The Lincoln Lodge 18 Aug 2025

Labor Day Sunday Funday Sunset Cruise!

Chicago Lakefront Cruises 31 Aug 2025

SIP & RNB Social: Labor Day weekend pre-party

VU Rooftop Bar 28 Aug 2025

Bearracuda Chicago: Labor Day Jockstrap Party!

The Jackhammer Complex 29 Aug 2025

POP UP SHOP - LABOR DAY WEEKEND

Da Dip 30 Aug 2025

Chicago Labor History Tour: Pullman/ Steel Makers 1:00 p.m.-5:00 p.m.

2301 S Prairie Ave 19 Sep 2025

Historic Pullman Labor History Tour - August 2025

Pullman Exhibit Hall 17 Aug 2025

Chicago Labor History Tour: Haymarket / Packingtown 8:30 a.m.-12:15 p.m.

2301 S Prairie Ave 19 Sep 2025

Lifestyle Boat party

chicago boat yacht rental 31 Aug 2025

Historic Pullman Labor History Tour - September 2025

Pullman Exhibit Hall 21 Sep 2025

Labor Day Pickleball Tournament at Clark Street Pickleball

2352 N Clark St, Chicago, IL 60614-3423, United States 1 Sep 2025

Afro Fusion Pop Up Edition [ Labor Day Edition]

Le Nocturne Chicago 31 Aug 2025

The Labor Day Edition of The Sky Affair House Music Day Party at Vu Rooftop

VU Rooftop. 22nd Floor 1 Sep 2025

La Vie: Afrobeats Day party at ROOF on theWit (Sunday Labor Day Weekend)

ROOF on theWit 31 Aug 2025

Chicago Labor History Tour: Haymarket / Packingtown 1:00 p.m. - 4:40 p.m.

2301 S Prairie Ave 19 Sep 2025

Chicago Labor History Tour: Pullman/ Steel Makers 8:30 a.m.-12:30 p.m.

2301 S Prairie Ave 19 Sep 2025

PATIO BEEF: BIG BEAR BBQ LABOR DAY

The SoFo Tap 1 Sep 2025

Ultimate Labor Day Black Party SNEAKER Edition 2025

Visions Chicago 16 Mar 2025

Litty in the City QB Tune up

10001 S Pulaski Rd 1 Sep 2025

Labor Day Weekend on The Oasis at Shore Club! ☀️🏖️

1603 N Lakeshore Dr, Chicago, IL, United States, Illinois 60611 30 Aug 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) 1 Sep 2025

The Saturday Night Cruise -R&B |Fireworks | Live DJ | Two Bars

Island Party Hut 10 May 2025

The Wednesday Night Cruise -R&B | Fireworks | Live DJ | Two Bars

Island Party Hut 7 May 2025

Chicago Steppers Homecoming

McCormick Place 28 Aug 2025