Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (June 19-22, 2025) including the best weekend events and activities.
(If you are planning ahead, you can also find the best things to do next weekend here.)
I suggest bookmarking this blog post as it is updated regularly with new events and activities.
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 Pride Fest – June 21-22, 2025
Magnificent Mile™ Art Festival – June 21-22, 2025
Vegandale Fest – June 21-22, 2025
The Lyrical Lemonade Summer Smash Festival – June 20-22, 2025
Gold Coast Greek Fest – June 20-22, 2025
Meltin Margs Music Festival at Soldier Field – June 20-21, 2025
Summer Nature Fest at the Peggy Notebaert Nature Museum – Friday, June 20, 2025, 4-8pm – Explore the museum after hours.
Full Moon Jam at Arrington Lagoon (Evanston) – Friday, June 20, 2025, 6-9pm | FREE
Chinese Dragon Boat Race at Ping Tom Memorial Park – Saturday, June 21, 2025, 8am-5pm | FREE Admission – Dragon boat race teams will compete on the south branch of the Chicago River in beautifully decorated dragon boats.
Pride Flotilla – Saturday, June 21, 2025, 1pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Juneteenth Annual Community BBQ at The DuSable Black History Museum and Education Center – Thursday, June 19, 2025, 8am-8:30pm – Education, entertainment, food, and local vendors honoring Black history, culture, and freedom.
Chicago’s African Fashion on the Runway at Field Museum – Thursday, June 19, 2025, 12-1:30pm
Juneteenth Celebration at La Follette (Robert) Park – Thursday, June 19, 2025, 1-6pm | FREE
West Town Night Market at Midwest Coast Brewing – Thursday, June 19, 2025, 4-9pm | FREE
Juneteenth Freedom Ride – Thursday, June 19, 2025, 6pm | FREE
CamelPhat at Navy Pier (18+) – Friday, June 20, 2025, 4pm
Trenzas de Agua: A Solstice by the Water at McKinley Park Lagoon – Friday, June 20, 2025, 5:30-6:30pm | FREE
3rd Fridays Free Admission Museum Night at Heritage Museum of Asian Art – Friday, June 20, 2025, 5–8pm
The Queery New Works Festival – Friday, June 20, 2025 – Hosted by PrideArts to showcase scenes from the Playwrights Lab. With the help of the audience, one piece will be selected to received a fully funded production at the end of their 25/26 season.
Sangria Fest on the Beach – Sangria Tasting at North Ave. Beach – Friday, June 20, 2025, 6-9pm
Zhou B Art Center 3rd Fridays – Friday, June 20, 2025, 7-10pm | FREE
Open Studios (3rd Fridays) at Bridgeport Art Center – Friday, June 20, 2025, 7-10pm | FREE
312 RiverRun 5K – Saturday, June 21, 2025, 10am-12pm
American Indian Summer Solstice at Schiller Woods-East – Saturday, June 21, 2025, 11am-1pm | FREE – Celebration of the sun’s power with dancing, storytelling and sun-themed art.
Juneteenth Beach Volleyball Tournament (Ages 21+) – Saturday, June 21, 2025, 11am-2pm
West Loop Pizza Crawl – Saturday, June 21, 2025, 11am-2pm
Juneteenth Celebration at Dan Ryan Woods Pavilion – Saturday, June 21, 2025, 12-6pm | FREE
Cake on the Lake with Steve Aoki at Navy Pier (18+) – Saturday, June 21, 2025, 4pm
Candlelight Concert: Rings and Dragons – Saturday, June 21, 2025, 6:30pm & 8:30pm
Ritmo del Mar at the Shedd Aquarium (21+) – Saturday, June 21, 2025, 7-11pm – Music, cuisine, culture and animals with an aquatic backdrop. Dance to the sounds of salsa, cumbia, merengue and Latin jazz. Food and beverages are available for purchase.
Summer Fireworks at Navy Pier – Saturday, June 21, 2025, 10-10:10pm | FREE
Fight For Air Climb at Soldier Field – Sunday, June 22, 2025, 8am-12:30pm
The Kibbitznest Comedy Club – Sunday, June 22, 2025, 7:30-9pm – Final summer show of pop-up comedy club.
FREE Community Pop-Up Thrift Boutique at Hermosa Neighborhood Association – June 21-22, 2025, 12-3pm
Alice’s Adventures in Wonderland by the Joffrey Ballet – Through June 22, 2025
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:
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 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.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Take a Lake Cruise
This weekend is expected to be very hot. Enjoy a cool lake breeze and admire the Chicago skyline from a lake cruise.
Look for Street Art
See Chicago’s many murals by joining a street art tour.
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.
Sensory Feast: A Magical Dining Experience
Have a unique dining experience at Sensory Feast: A Magical Dining Experience. Cutting-edge projection mapping transforms your table into a living canvas where mystical adventures come to life while you enjoy a 3-course meal.
When: Every Friday and Saturday in June
Where: The Metropolitan, 233 S Wacker Dr 67th Floor, Chicago, IL 60606
Cost: General admission is $125 per person. Click here for full prices and to purchase tickets in advance.
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.
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 in June.
