Spending Labor Day Weekend in Chicago? This is a great time to enjoy festivals, lakefront fun, and end-of-summer energy.
As a Midwest local, I’ve got you on the best tips and activities in the city over Labor Day weekend this year!
Most locals make their way home to family barbecues, so this weekend is a quieter time to visit and you can expect fewer crowds.
Don’t worry- the windy city is always lively! You just have a bit more space to yourself.
Some of the best things to do in Chicago over Labor Day Weekend include catching a Chicago Cubs game, attending a Labor Day Parade, enjoying a local music festival, a fireworks show at Navy Pier, and taking a Chicago Architecture Cruise.
11 Best Things to Do in Chicago for Labor Day Weekend
1. Chicago Baseball
Chicago locals take Chicago sports seriously. You’re in luck!
The Cubs have a home game this year against the Atlanta Braves at Wrigley Field on Monday, September 1, 2025.
I love the atmosphere at Cubs games. Everything is so lively, from the stadium to neighboring Gallagher Way and the Wrigleyville Neighborhood.
There are so many things to do when there is so much cheer and excitement around you!
Grab tickets, soak up the stadium energy, and explore Wrigleyville after the game.
It’s one of the best ways to enjoy summer’s final weekend in the city!
2. Parades
The Chicago Labor Day Parade celebrates workers with music, floats, and community groups.
It’s smaller than other city parades, but still a fun, local way to honor the holiday.
Check the city’s events calendar for updated start times and parade route details.
3. Music Festivals
Labor Day Weekend in Chicago is packed with music festivals!
- North Coast Music Festival takes place at SeatGeek Stadium in Bridgeview.
It features big-name EDM, hip-hop, and pop acts, along with immersive art and light shows.
- ARC Music Festival at Union Park brings top house and techno DJs from around the world.
It’s popular with electronic music fans and offers a stylish urban vibe - The Chicago Jazz Festival is a free, multi-day event held in Millennium Park.
It features local and international jazz musicians on outdoor stages, with lawn seating and skyline views.
⭐Popular Chicago Hotels
4. Cultural Events
Chicago’s Jefferson Park neighborhood is known to have some of the most authentic Polish food in the city!
It also hosts the annual Taste of Polonia Festival.
Enjoy Polish food, music, and dance performances. It’s a family-friendly event with strong local roots.
I love Smakosz Restaurant in Jefferson Park. It is a small, family-owned business with the best traditional Polish food.
My pierogies here were 10/10!
5. Chicago Architecture Cruise
The Chicago Architecture Cruise remains a favorite tour among locals and tourists.
Take a guided cruise on the Chicago River for great skyline views and quick stories behind the city’s buildings.
It’s a relaxed, scenic way to explore the city. I honestly can’t believe I haven’t taken this tour myself yet- it’s always at the top of my list!
It’s a great activity even if you only have 1 day in Chicago!
6. Navy Pier Fireworks
Navy Pier is famous for their free summer Fireworks shows!
I love watching the dazzling fireworks over Chicago’s Skyline- it just adds to the joy of the city.
Catch the final summer fireworks show of the season at Navy Pier on Saturday night.
It’s free and visible from across the lakefront.
A classic Chicago way to wrap up the season.
7. Chicago Riverwalk
The Chicago Riverwalk stretches around 1 mile along the downtown riverfront and is one of the best places to enjoy the city!
Strolling the Riverwalk is one of my favorite things to do in Chicago.
Walk along the water, stop at restaurants like City Winery or Tiny Tapp, or grab drinks on a floating barge.
There are kayak rentals, public art installations, and plenty of spots to sit and people-watch.
It’s scenic during the day and especially beautiful at night when the buildings light up!
8. Free Walking Tour
Join a free walking tour to learn about the city’s neighborhoods and history.
Tours are often tip-based and cover downtown or local spots like Lincoln Park.
Popular Chicago Tours
9. Beach Day
Chicago beaches close for the season after Labor Day.
Lifeguards are on duty through Monday, September 1.
Head to North Avenue or Montrose Beach for swimming, sunbathing, and volleyball.
10. Bike Lakeshore Trail
The Lakefront Trail stretches 18 miles along the lake, passing beaches and parks, making it perfect for a scenic bike ride any time of day.
Ride past beaches, parks, and skyline views. Mornings and evenings are best to avoid the heat and crowds.
You can rent bikes from Divvy bike-share stations located throughout the city, including near the lakefront.
Divvy charges a $1 unlock fee plus about 19 cents per minute, with day passes available for around $18 that allow unlimited rides up to 3 hours each.
For longer or more specialized rentals—like e-bikes or tandems—local shops such as Bike and Roll and Bobby’s Bike Hike offer hourly and daily rates.
11. Millennium and Grant Park
Millennium Park and Grant Park are two of Chicago’s most famous green spaces.
Walking the parks is one of my favorite free activities in the city. Walk, bike, or settle down with a picnic and book while enjoying the city come to life around you.
The top features of Millennium Park include the iconic Bean sculpture, Lurie Gardens, and skyline photo ops.
Grant Park is a short walk away. Its main feature is the Buckingham Fountain. You can also see Lake Michigan from here.
Both parks are prime spots in the Downtown City Center.
Tip: The parks are located next to the Chicago Art Institute, if you would like to museum hop after!
Conclusion
Labor Day Weekend is your last chance to enjoy summer in Chicago.
From festivals and parades to beaches and baseball, the city offers something for everyone.
Plan your trip now to catch the best events, soak up the lakefront, and make the most of this vibrant weekend before the season ends.
Don’t wait—Chicago’s Labor Day weekend won’t disappoint!
