Spending Labor Day weekend in Chicago and looking for things to do? You are in luck because Labor Day weekend (August 29-September 1, 2025) is a great time to visit Chicago. There are tons of fun things to do in Chicago on Labor Day and even more during Labor Day weekend.
I suggest bookmarking this blog post as I will be updating this travel blog post regularly with new events and activities as they are announced.
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Things to Do in Chicago on Labor Day Weekend
Here are the best things to do in Chicago during Labor Day weekend including the best weekend events and festivals.
Attend an Outdoor Festival
Enjoy food, live music and other fun activities at an outdoor festival. Outdoor festivals taking place in Chicago during Labor Day weekend include: Chicago Jazz Festival (August 29–September 1), ARC Music Festival (August 30–September 1), North Coast Music Festival (August 29–31, 2025), Inaugural House Music Parade and Festival (August 31), Villapalooza (August 31), West Loop Art Fest (August 31–September 1), Taste of Polonia Festival (August 30–September 2) and Bitter Jester Music Festival at Navy Pier (August 30 – September 2).
See the Last Summer Fireworks Show (Plus Summer Celebration Drone Show) at Navy Pier
See the last free fireworks show of the summer season at Navy Pier on Saturday, August 31 at 10pm.
In addition to fireworks, Navy Pier is putting on a special free summer celebration drone show right before the usual fireworks show (from 9:45-10:00pm). The drone show will feature more than 300 synchronized drones creating, colorful, illuminated images across the sky.
While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront.
The most relaxing way to watch the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
Join a Labor Day Party Cruise
Join a Labor Day themed booze cruise and party on the “Summer Of George” boat with music and and a festive atmosphere:
Labor Day Sunday Sunset Booze Cruise – Sunday, September 1
Swiftie Party Cruise! – Sunday, September 1
Take an Architecture River Cruise
Taking an architecture river cruise is a must on any Chicago bucket list.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is a fun activity whether in the day, around sunset and in the evening. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views especially around sunset and a refreshing cool lake breeze.
If your time is short, you can do a combination river and lake cruise.
Go Kayaking
A fun way to explore the city is to go kayaking in the Chicago River or the lake. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders and you can choose between day tours, sunset tours and fireworks tours.
You can rent kayaks at Ohio Street Beach here.
Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Have Fun at Navy Pier
Navy Pier is a must do if you are visiting Chicago with toddlers or young kids.
Check out the new Flyover Chicago, an immersive flyover experience.
Other fun attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), restaurants, shops and the Chicago Children’s Museum.
In addition to Navy Pier’s attractions, visitors can also enjoy live music as part of the Live on the Lake!, an outdoor music series.
Spend Time at the Beach
Spend time at one of Chicago’s many beaches before they officially close. If you are thinking of getting in the water to cool down, you can check the swimming conditions here.
Walk or Bike the Lakefront Trail
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. During Labor Day weekend, the lakefront will be packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see the Chicago skyline, people watch and get some exercise.
Here is a map of the trail as well as its access points.
Hang Out on the Riverwalk
The Chicago Riverwalk along the south bank of the Chicago River is one of the best spots in Chicago for people watching. There are restaurants, bars, shops and places to sit along the way -see a map here.
The Big Bounce America
The Big Bounce America, the world’s largest traveling inflatable park, is only in the Chicago area for 2 weekends. There are separate areas in the park depending on age: toddlers (under 3), young kids (ages 3-7), bigger kids (ages 8-15) and adults (ages 16+).
Where: Skokie Sports Park, 3459 Oakton Street, Skokie (about 15 miles from downtown Chicago)
Cost: A 3 hour session is $35 for kids and $45 for adults.
Titanic: The Exhibition
Titanic: The Exhibition is in the Chicago suburbs for a limited time run. This interactive experience allows you to step inside recreations of the Titanic’s interior. Immerse yourself in the stories of its passengers, see hundreds of artifacts, and discover the tale of the design, creation, launch, maiden voyage, and tragedy of the historic ship.
Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
Look for Street Art
Looking for a unique thing to do this weekend? Walk around Chicago looking for street art.
One of the most famous Chicago murals is “Moose Bubblegum Bubble” by Jacob Watts which located at 33 E. Congress (South Wall). This famous mural is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions.
Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and more on this street art tour.
Watch a Baseball Game
Chicago is known for their love of sports, including baseball. You don’t need to be a baseball fan to enjoy a game – it is fun to just soak in the atmosphere.
Both the Chicago White Sox and the Chicago Cubs are playing home games during Labor Day weekend.
Friday, August 30 – Chicago White Sox vs. New York Mets at Guaranteed Rate Field (with post game fireworks)
Saturday, August 30 – Chicago White Sox vs New York Mets at Guaranteed Rate Field
Sunday, September 1 – Chicago White Sox vs New York Mets at Guaranteed Rate Field
Monday, September 2 – Chicago Cubs vs. Pittsburgh Pirates at Wrigley Field
More Chicago Labor Day Weekend Events
Other events taking place in Chicago Labor Day weekend include: Pearl Jam Dark Matter World Tour at Wrigley Field (August 29 & 31), Chi Food Truck Fest (August 30), Fridays on Fulton (August 30), Chicago Labor Day Parade (August 31), Lucha Libre in the Park (August 31), AVP Gold Series Chicago Open (August 30 – September 1), Fifth Third Bike the Drive (September 1) and WOOGMS Labor Day Parade (September 2).
As you can see there are many things to do in Chicago on Labor Day weekend. If you are looking for things to do during the week, here are more things to do in August and September.
What to Pack for Chicago for Labor Day Weekend
For out of town visitors, please note that the weather in Chicago during Labor Day weekend is usually hot and humid. Here are essentials things to pack for Chicago this Labor Day weekend.
• Comfortable walking shoes – Chicago is a very walkable city so you will probably do a lot of walking
• Reusable water bottle – It is usually hot and humid on Labor Day weekend so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella in case it rains
• Light sweater (and scarf) – For cool nights, indoor places with too much air conditioning and lake cruises
• Waterproof case – For your phone if you plan to go kayaking or spend time in the water
• External battery for your phone – To recharge your phone’s battery when you are outdoors
• Mosquito repellent – If you plan to be outside around dusk or at night.
• Sunscreen – A must if you will be spending a lot of time outside in the day
• Bathing suit and other beach essentials (if you are planning to spend time at the beach)
If you forget to bring something essential, don’t worry. There are many stores located close to the popular tourist attractions if you need to pick something up.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
