The arrival of summer in Chicago is nothing short of exuberant, and this weekend heralds the first full swing of the season.
As rooftops buzz with excitement, beaches offer refreshing sangrias, and fireworks light up the lakefront, the city opens up to a plethora of activities, from Pride celebrations in Northalsted to soulful tributes at City Winery.
Among the standout events is Black Yacht Weekend 2025, taking place from June 19 to 22 across multiple locations in Chicago.
Billed as the ultimate summer gathering, this four-day event is a celebration of community, culture, and the luxury of life on the water.
Set against the stunning Chicago skyline and the vibrant waters of Lake Michigan, Black Yacht Weekend promises an unforgettable experience blending boating, nightlife, networking, and opulent leisure.
Attendees will enjoy exclusive yacht parties, rooftop events, and the chance to connect with Black professionals, entrepreneurs, creatives, and influencers.
This inclusive experience is designed for all, whether you’re attending solo, with friends, or part of a larger group.
On Friday, June 20, revelers can kick off the weekend at the Sangria Fest on North Ave. Beach in the evening, where they can savor lakefront views with endless pours of red, white, and tropical sangrias.
For fans of soulful music, the Prince Experience is set to electrify the House of Blues at 7 p.m., while City Winery Chicago will host two shows featuring Dwele, the Detroit-born soul singer renowned for his silky vocals and timeless grooves at 6 p.m. and 9:30 p.m.
On Saturday, June 21, the celebration continues with the Forest Preserves’ Juneteenth Jubilee at Sand Ridge Nature Center from 11 a.m. to 3 p.m.
This delightful gathering will feature storytelling, soul food, genealogy workshops, and drum circles, making it one of the region’s most joyful and informative outdoor celebrations.
The Vegandale Festival at Butler Field in Grant Park is another highlight, where attendees can explore over 100 vegan vendors while enjoying high-energy music throughout the day.
Chicago Pride Fest also kicks off its first day, offering live music on multiple stages and drag performances in the Northalsted area.
Additionally, historian Bernard Turner will host a session titled “Juneteenth, the Great Migration & Bronzeville” from 11 a.m. to noon at 70 E. Pershing Rd., sharing stories of migration and legacy.
The West Pullman Juneteenth Festival starts at 1 p.m. at 821 W. 115th St., featuring music, food from Black-owned restaurants, and workshops focusing on housing and small business development.
Another community event, “Juneteenth in the Burbs!” will take place at Harper College from 2 p.m. to 6 p.m.
Guests can enjoy live jazz, youth talent, poetry, and a Freedom Exhibit with free books, food, and opportunities to engage with Black professionals.
Those looking for a vibrant evening can witness Navy Pier’s spectacular fireworks display at 10 p.m., marking a perfect end to the day’s festivities.
On Sunday, June 22, the Soul Brunch at City Winery offers a tribute to Chicago soul, featuring live performances that pay homage to legendary artists while guests enjoy a gourmet brunch spread starting at noon.
The second day of the Chicago Pride Fest will continue to celebrate with more music, drag, dancing, and festivities in the iconic neighborhood.
Day two of the Vegandale Festival at Butler Field promises just as much deliciousness as its first day.
Additionally, the Juneteenth Jamboree at Roots Handmade Pizza in the South Loop from 3 p.m. to 9 p.m. invites guests aged 21 and up to dance, mingle, and celebrate Black joy with DJs and drinks.
Finally, wrapping up the weekend on Monday, June 23, is a must-see performance by The Floacist from Floetry at City Winery at 7 p.m., who will make her solo U.S. debut showcasing a blend of spoken word and heart.
With a diverse and exciting lineup of events, Black Yacht Weekend 2025 promises to be a highlight of the summer season in Chicago.
image source from：chicagodefender
