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 3-5, 2022) 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.

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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 do a lot of walking
Reusable water bottle – It will be hot and humid this weekend so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella -There is a chance of rain this weekend
• Light sweater (and scarf) – For night, lake cruises, indoor places with cold AC
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 plant 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.

Chicago Labor Day Weekend 2022 Events

Bike the Drive

Grab your bike for a car-free ride on the recently-renamed Jean Baptiste Point DuSable Lake Shore Drive while enjoying views of the lake and skyline. During 20th 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 5, 2021 5:30AM – 10:00AM

Where: The main festival and starting location is at Butler Field in Grant Park (235 S Columbus Dr). Cyclists can enter from one of five designated entry points along the road.

Cost: General Admission is $60 for adults and is only offered for a limited time. Day of admission is $70. Youth is always $18.

Roscoe Village Burger Fest

Roscoe Village Burger Fest returns for its 14th year this September. In addition to burgers from various Chicago eateries, you can find two stages of music, arts & crafts and the action-packed “Kids Zone” area. Visitors will also have the opportunity to vote for Chicago’s Best Burger.

When: Friday, September 3, 2021 through Sunday, September 5, 2021

Hours:  5pm to 10pm on Friday and 11am to 10pm on Saturday & Sunday

Where: 2000 W Belmont Ave. (corner of Belmont and Damen)

Cost: $10 suggested fest donation

Sundays on State

Chicago Theatre instagram photo spot

State Street from Madison to Lake is transformed into an open street this Sunday. This portion of State Street will be closed to vehicle traffic for a free, interactive block party to give pedestrians a chance to experience arts and culture, active recreation, retail, restaurants, and bars against the backdrop of State Street’s iconic architecture like the Chicago Theatre (one of the best Chicago photo spots).

When: September 5 from 11 a.m.-8 p.m. Click here for more information.

Listen to Free Music at Millennium Park

Enjoy being outside while listening to free musical performances at the Jay Pritzker Pavilion in Millennium Park.

Friday, September 3, 5:30–8:30pm – Chicago In Tune — Gospel Music
Saturday, September 4, 5:30–8:30pm – Chicago In Tune — Jazz
Monday, September 6, 6:30–8:30 pm – “Contemporary Indigenous Voices” (part of Millennium Park Summer Music Series

Maxwell Street Market

Head to Maxwell Street Market for flea market shopping and some of the best street food in Chicago.

From 11am-2pm there is also Jazz Music Celebration presented as part of Chicago In Tune with co-host James Sanders & Conjunto + The Herbsaint Band.

Where: 800 S. Desplaines St., Chicago, IL 60607

When: Sunday, September 5, 2021 9am–3pm  

Cost: Admission is free

Watch Free Movies in the Park

You can watch free movies on Friday, September 3 and Saturday, September 4, 2021 in a few Chicago public parks through the Movies in the Parks. Movies start at 8:00pm.

Watch Shakespeare in the Park

Watch an outdoor performance of DREAM (a fresh spin on Shakespeare’s “A Midsummer Night’s Dream”) at Ping Tom Memorial Park in Chinatown. Part of the Chicago Shakespeare in the Parks this multilingual performance is fun for all ages. Seating area surrounding the stage is limited. 

When: Saturday, September 4 starts at 6:00 p.m

Where: Ping Tom Memorial Park, 1700 S. Wentworth Ave  (Tip: Consider taking the water taxi to Chinatown- it is more relaxing and picturesque way than taking the El)

Cost: Free

More Labor Day Weekend Events

Other festivals and events taking place this Labor Day weekend include: ARC Music Festival (September 4-5, 2021), North Coast Music Festival (September 3-5, 2021), AVP Gold Series, Chicago Open (September 3-5, 2021) and Pitchfork Music Film Series.

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 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.


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.

Spend Time at the Beach

Spend time at one of Chicago’s many beaches.  If you are thinking of getting in the water to cool down in the summer, 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 at 9:00 & 9:30 p.m. 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 are looking to avoid the heat and side, Art Institute of Chicago (111 S Michigan Ave) is one of Chicago’s best indoor attractions and one of top museums in the world. September 6, 2021 is the last date to see the popular Bisa Butler: Portraits exhibition of Bisa Butler’s portrait quilts which vividly capture personal and historical narratives of Black life.

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

See the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork. Tickets must be purchased online in advance and they are selling quickly! There are also yoga sessions which include a 35 minute Yoga class + 45 minutes thereafter to enjoy the exhibit.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago, IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

See The Art of Banksy Exhibit

“The Art of Banksy” Exhibit is the largest touring exhibition of authentic Banksy artworks in the world. The exhibit will feature over 80 original works from private collectors across the globe, offering a rare opportunity to view authenticated and certified Banksy artworks rarely seen by the general public including iconic works such as ‘Girl and Balloon’, ‘Flower Thrower’ and ‘Rude Copper’ alongside some of Banksy’s lesser known masterpieces. On display are prints, canvasses, screenprints, sculptures, unique works and limited-edition pieces mainly dated between the years 1997 to 2008, the period which resulted in Banksy’s most recognisable and well-known works.

This exhibition is not authorized by Banksy nor is it curated in collaboration with the artist but sourced from private collections allowing the public to see works that would otherwise stay hidden in private homes or warehouses.

Where: 360 N. State St, Chicago, IL 60654

Cost:  Tickets prices range from $39.99 to $99.99 for adults and $29.99 for children 6-16 years old (plus $6.85 service fee). See https://banksyexhibit.com/chicago/buy-tickets for full prices and to purchase tickets in advance.

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.

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.

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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