Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago during Labor Day weekend (September 4-7, 2026) including the best events and activities.
{If you are planning ahead, you can also find the best things to do next weekend here.)
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.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Chicago Jazz Festival – September 3-6, 2026 | Free Admission
The Great American Lobster Fest – September 5-6, 2026, 1-8pm | Free
Taste of Polonia Festival – September 4-7, 2026
ARC Music Festival – September 4-7, 2026
North Coast Music Festival – September 4-6, 2026
Sound & Gravity Festival – September 3-6, 2026
Fiesta Boricua: De Bandera a Bandera – September 5-6, 2026, 12-9pm | Free
African Festival of the Arts (Washington Park) – September 5-7, 2026
Flutter into Fall at Peggy Notebaert Nature Museum – Saturday, September 5, 2026, 10am-2pm – Annual celebration of their butterflies as the monarchs begin their migration.
Chicago Labor Day Parade & Eddie Fest – Saturday, September 5, 2026, 11am | Free
Bike the Drive – Sunday, September 6, 2026, 6:30am
Piano Men: A Billy Joel & Elton John Tribute at AIRE Rooftop – Sunday, September 6, 2026, 5pm & 8pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
First Friday Music Series (Rogers Park) – Friday, September 4, 2026, 6-8pm – Evening of live music on Sheridan Rd. between Devon and Pratt.
Level Up: Anime at the Museum (Field Museum) – Friday, September 4, 2026, 5:30-8:30pm
West Town First Fridays – Friday, September 4, 2026, 6-8pm | Free
Hippo Campus at Gallagher Way – Friday, September 4, 2026, 7pm
Millennium Park Free Summer Workout – Saturday, September 5, 2026, 8-9:45am | Free Admission – Last workout of the summer.
IndigiFest: Celebrating Indigenous Culture at Grant Park – Saturday, September 5, 2026, 11am-5pm | Free
An Idiot’s Guide to Wine – Saturday, September 5, 2026, 6pm & 8:30pm
Big Ten Watch Party at Gallagher Way – Saturday, September 5, 2026, 10:30am-10pm
Paint the Chicago Skyline – Saturday, September 5, 2026, 3-5pm
Wild Mile Projections: Special Edition! – Saturday, September 5, 2026, 9-9:30pm | Free – Collaboration between Urban Rivers and the School of the Art Institute of Chicago featuring a collection of past projections displayed at the Wild Mile.
Wekfest at Navy Pier – Sunday, September 6, 2026, 1-6pm
Bottomless Margaritas on the Riverwalk (Ages 21+) – Sunday, September 6, 2026, 3-5pm
Night Out In The Parks: Reclaimed Timber (Wild Mile) – Sunday, September 6, 2026, 7:30-8:30pm | Free
Bottomless Mimosas on the Riverwalk (Ages 21+) – September 5 & 6, 2026, 11am-1pm
Live on the Lake! at Navy Pier – September 4-7, 2026 | Free
Pilates at Gallagher Way – Monday, September 7, 2026, 7-8am | Free
Chicago History Museum Free Day for Illinois Residents – Monday, September 7, 2026 | Free
CorePower Yoga Pop-Up Class at Gallagher Way – Monday, September 7, 2026, 5:30-6:30pm | Free
Tango Dancing at Gallagher Way – Monday, September 7, 2026, 7-10pm | Free
SAW The Musical: The Unauthorized Parody of SAW – Through September 6, 2026
Hell in a Handbag Productions Presents Joan Crawford Goes To Hell at The Clutch – Through September 27, 2026
More Things to Do in Chicago This Weekend
In addition to the weekend events listed above, below are more of the best things to do in Chicago this weekend:
Join a Labor Day Party Cruise
Join these Labor Day themed booze cruises and party on a boat with music and a festive atmosphere:
Saturday Night Labor Day Fireworks Booze Cruise – Saturday, September 5, 2026
Swiftie Booze Cruise Labor Day Weekend – Sunday, September 6, 2026
Labor Day Weekend All White Attire Party Cruise – Sunday, September 6, 2026
Labor Day Cruise on Lake Michigan – Monday, September 7, 2026
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.
Watch Fireworks
See the last free fireworks show of the summer season at Navy Pier on Saturday, September 5, 2026 at 10pm.
The fireworks can be seen from various spots along the Lakefront including North Avenue Beach, Oak Street Beach and the Adler Planetarium Skyline Walk.
The best and most relaxing way to see the Navy Pier fireworks show is on a fireworks lake or river cruise.
If you enjoy guided tours, you can also see the fireworks and other attractions on this fireworks segway tour.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Take a Lake Cruise
Enjoy a cool lake breeze and admire the Chicago skyline from a lake cruise.
If your time is short, you can do a combination river and lake cruise.
Kayak in the River or Lake
A fun way to explore the city is to go kayaking in the Chicago River or Lake Michigan. You can rent a kayak in the Chicago River here and Ohio Street Beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this weekend include:
Tribute to Lauryn Hill
Coldplay vs. Imagine Dragons
90s Hip-Hop on Strings
You can find the full list of candlelight concerts in Chicago here.
Titanic: A Voyage Through Time
Step into history at Titanic: A Voyage Through Time an extraordinary virtual reality (VR) journey into history’s most famous ship. Dive to the wreckage as it rests today, then travel back to 1912 to experience the Titanic as a passenger. Walk the Grand Staircase, meet the people who shaped its story, and witness history firsthand in this immersive adventure.
When: Through September 27, 2026
Where: 108 West Germania Place, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Minecraft Experience: Villager Rescue
Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
Watch a Drunk Shakespeare Play
Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.
Where: The Lounge At The Lion, 182 North Wabash Avenue
Cost: Prices start at $29 per person. Click here to purchase tickets.
Take a Spray Paint ‘n’ Sip Urban Art Workshop
Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.
Where: Studio W.I.P. – Uptown, 1047 W Lawrence Ave, Chicago, IL 60640
Cost: $45 per person for adults. Click here to purchase tickets.
Wondra: Immerse yourself in the magic of nature
Looking for a fun activity for kids? Head to the suburbs for Wondra, where each space invites curious minds to discover hidden details, dazzling colors, and natural awe-scapes that spark imagination and evoke wonder. Experience nature’s wonders in a whole new light with this immersive journey.
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets in advance.
As you can see there are many things to do in #Chicago this weekend. If you are looking for more things to do in the Chicago area, you can find the best things to do in the suburbs here. If you are looking for things to do during the week, you can find more things to do in Chicago this week here and the best things to do in Chicago in September here.
