BEST Things do in Chicago on Labor Day Weekend

Spending Labor Day weekend in Chicago and looking for things to do? You are in luck because Labor Day weekend (September 1-4, 2023) 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 plan to update it regularly with any new events and information.

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, 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 night, lake cruises and indoor places with too much air conditioning
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 more fun things to do in Chicago on Labor Day weekend

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


Join a Labor Day Booze Cruise

Want to drink while enjoying being on the water? You can join several Labor Day themed booze cruises including this daytime booze cruise or this sunset booze bruise.

When: Sunday, September 4 (4:00 p.m or 7:30 p.m.)

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.

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 can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. There are 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.

Navy Pier is also the starting point for various sightseeing tours and cruises.


Watch Free Fireworks at Night

Navy Pier puts on free summer fireworks shows every Wednesday and Saturday night in the summer through Labor Day weekend. You can watch the last fireworks show of the summer season on Saturday, September 2, 2023.

While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront. Another great option for watching the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.

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.

You can also rent kayaks, jet skis and boats at various beaches to get out on the lake. 

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.

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Push Pin Travel Maps

Walk Through a Sunflower Field

Visiting sunflower fields was a popular activity for Chicagoans this summer. Many sunflower fields and mazes are still in bloom and open for visitors on Labor Day weekend. Here is a list of the best sunflower fields near Chicago with locations, dates, hours, prices and all the information you need to plan your visit.

Go Apple Picking

Looking for a fun outdoor activity in the Chicago area? Take a day trip to a nearby apple orchard to go apple picking or indulge in fresh apple cider donuts. There are many apple orchards are located in the Chicago suburbs about an hour or less from downtown. Some apple orchards also offer kid friendly attractions and activities like corn mazes, kid farms and more.

Here is a list of the best apple orchards near Chicago for apple picking with locations, dates, hours, prices and all the information you need to plan your visit.

Attend an Outdoor Festival

Enjoy food, live music and other fun activities at an outdoor festival. Outdoor festivals taking place in Chicago Labor Day weekend include: ARC Music Festival (September 1-3, 2023), North Coast Music Festival (September 2-4), Great American Lobster Fest (September 2-4), West Loop Art Fest (September 3-4), Fiesta Boricua Festival (September 3-4), Taste of Polonia Festival (September 2-5), Lincoln Square Greek-Fest (September 2-5), Sundays on State (September 4), and Bitter Jester Music Festival (at Navy Pier) (September 5).

Chicago Labor Day Weekend Events

Chicago Jazz Festival

Chicago Jazz Festival is presenting four days of music at the Jay Pritzker Pavilion and one more location at Millennium Park — plus the return of neighborhood events. Visit ChicagoJazzFestival.us for more information.

When: September 1–4

Where: Citywide and in Millennium Park

Cost: FREE Admission

Bulls Fest

Bulls Fest is a new weekend-long Chicago street festival outside the United Center featuring a 3v3 tournament, live music, local food, art, and more. There will be family-friendly activities as well as youth skills clinics on Saturday and Sunday.

When: September 3-4

Where: Bulls Fest will take place primarily outside the United Center in the parking lots on the north side of the arena, as well as along Madison Street between Wood Street and Damen Avenue.

Cost: Bulls Fest is FREE to the public. 3v3 Tournament participants will pay a team entrance fee to compete.

Bike the Drive

Grab your bike for a car-free ride on Jean Baptiste Point DuSable Lake Shore Drive while enjoying views of the lake and skyline. During the annual Fifth Third Bike the Drive, the 30-mile stretch from Bryn Mawr Ave to the Museum of Science and Industry is completely closed to cars and open only to bikes. Ride as little or as much of the 30-mile course as you’d like and then enjoy a post-ride festival in Grant Park. Rentals are available if you don’t have a bike. Proceeds from the event support the Active Transportation Alliance, a non-profit advocacy organization working to improve conditions for walking, biking, and public transit throughout Chicagoland.

When: Sunday, September 4

Where: The main festival and starting location is at Butler Field in Grant Park (235 S Columbus Dr).

Free Millennium Park Summer Workout

Want to join free yoga (and other exercise classes) while also spending time outside? The Millennium Park Summer Workouts program ends on Saturday before Labor Day weekend. The program offers series of free 45-minute workouts at Millennium Park Great Lawn as follows.

8–8:45am – Tai Chi
9–9:45am – Yoga
10–10:45am – Pilates
11–11:45am – Zumba®

When: Saturday from 8-11:45am.

Where: Great Lawn at Millennium Park

More Chicago Labor Day Weekend Events

Other events taking place in Chicago Labor Day weekend include:
AVP Gold Series Chicago Open, Logan Square’s Annual Lucha Libre Wrestling Match and First Annual Bags Brawl at Gallagher Way.

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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