BEST Things do in Chicago on Labor Day Weekend 2024

Spending Labor Day weekend in Chicago and looking for things to do? You are in luck because Labor Day weekend (August 30, 2024 – September 2, 2024) 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.

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

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 drugstores located close to the popular tourist attractions if you need to pick something up.

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 2024 include: Chicago Jazz Festival (August 29–September 1, 2024), ARC Music Festival (August 30–September 1, 2024), North Coast Music Festival (August 30–September 1, 2024), Inaugural House Music Parade and Festival (August 31, 2024), West Loop Art Fest (August 31–September 1, 2024) and Taste of Polonia Festival (August 30–September 2, 2024).

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    Watch Free Fireworks at Night

    Watch the last free fireworks show of the summer season at Navy Pier on Saturday before Labor Day.

    While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront.

    You can see the fireworks and explore Chicago at night on this fireworks segway tour.

    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.

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    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 and a refreshing cool lake breeze. Lake cruises depart from Navy Pier or the Michigan Avenue bridge. If your time is short, you can do a combination river and lake cruise.

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    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, 2024

    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

    outdoor rides at Navy Pier Chicago

    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.

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    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 lakefront

    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

    best things to do chicago travel blog

    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.

    Watch Digital Art at Art on theMart

    Art on the Mart
    Looking for a unique thing to do at night? Check out Art on theMART, the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown nightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

    Bouncy Games

    The Bouncy Games ending its limited time experience in Chicago in September. This large inflatable course is full of giant slides and obstacle courses for kids 3+.

    Where: Exhibition Hub Art Center Chicago, 2367 W Logan Blvd, Chicago, IL 60647

    Cost: Price varies. Children ages 3 and under enter free of charge. Click here for full prices and to purchase tickets in advance.

    Visit the Art Institute of Chicago

    The Art Institute of Chicago in one of the best Chicago indoor attractions

    If you want to avoid the heat and sun, Art Institute of Chicago (111 S Michigan Ave) is one of Chicago’s best indoor attractions and one of top museums in the world.

    Click here to buy a skip the line ticket if you want to avoid long lines.

    Look for Street Art

    Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

    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

    wrigley field Chicago

    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 2024 weekend.

    Friday, August 30, 2024 – Chicago White Sox vs. New York Mets at Guaranteed Rate Field (with post game fireworks)
    Saturday, August 30, 2024 – Chicago White Sox vs New York Mets at Guaranteed Rate Field
    Sunday, September 1, 2024 – Chicago White Sox vs New York Mets at Guaranteed Rate Field
    Monday, September 2, 2024 – Chicago Cubs vs. Pittsburgh Pirates at Wrigley Field

    Titanic: The Exhibition

    Titanic: The Exhibition is ending its limited time run in the Chicago area on Labor Day weekend. 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.

    Downton Abbey: The Exhibition

    Downton Abbey: The Exhibition is ending its limited time run in the Chicago area on Labor Day weekend. Delve deep into the post-Edwardian era with never-before-seen treasures, from original costumes to iconic props, and exclusive series footage. Traverse the grandeur of the Crawley estate, from the bustling kitchen to the opulent dining room. Explore British society, culture, and fashion amidst historical upheavals.

    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.

    More Chicago Labor Day Weekend 2024 Events

    Other events taking place in Chicago Labor Day 2024 weekend include: Chi Food Truck Fest (August 30, 2024), Fridays on Fulton (August 30, 2024), Chicago Labor Day Parade (August 31, 2024), Lucha Libre in the Park (August 31, 2024), Fifth Third Bike the Drive (September 1, 2024), Swiftie Party Cruise! (September 1, 2024), AVP Gold Series Chicago Open (August 30 – September 1, 2024) and Live on the Lake! at Navy Pier (August 30 – September 2, 2024).

    As you can see there are many things to do in Chicago on Labor Day weekend.

    Planning a trip to #Chicago? Check out my Chicago guides and itineraries:



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