Black Yacht Weekend
Summer in Chicago doesn’t tiptoe in—it kicks the door open. With the solstice now behind us, this weekend marks the season’s first full swing. Rooftops are buzzing, beaches are pouring sangria, and the lakefront lights up with fireworks. From Pride in Northalsted to soul tributes at City Winery, from Black Yacht Weekend to vegan eats in Grant Park, the city is wide open. If you’re stepping out, here’s where the action is.
All Weekend
Black Yacht Weekend 2025
June 19–22 | Multiple locations across Chicago
Black Yacht Weekend 2025 is billed as the ultimate summer event celebrating community, culture, and the luxury of life on the water. Set against the Chicago skyline and the vibrant waters of Lake Michigan, this four-day event offers a unique experience blending boating, nightlife, networking, and unparalleled luxury. From exclusive yacht parties to rooftop events, Black Yacht Weekend brings together Black professionals, entrepreneurs, creatives, and influencers for an unforgettable weekend of fun, relaxation, and connection.
Whether you’re attending solo, with friends, or as part of a group, Black Yacht Weekend is designed to be an inclusive experience for everyone.
Friday, June 20
Sangria Fest on the Beach
North Ave. Beach | Evening
Unwind with lakefront views and endless pours of red, white, and tropical sangrias. A sunset, a breeze, a glass—what more do you need?
The Prince Experience
House of Blues | 7 p.m.
A tribute show that channels the spirit of Prince with energy, sequins, and soul. Come dressed ready to dance.
Dwele Live (2 Shows)
City Winery Chicago | 6 p.m. & 9:30 p.m.
The Detroit-born soul singer brings his silky vocals and timeless grooves to the intimate City Winery stage for a night of grown folks’ music.
Saturday, June 21
Forest Preserves’ Juneteenth Jubilee
Sand Ridge Nature Center, South Holland | 11 a.m.–3 p.m.
Storytelling, soul food, genealogy workshops, and drum circles—this is one of the region’s most joyful and educational outdoor Juneteenth gatherings.
Vegandale Festival
Butler Field, Grant Park | All Day
100+ vegan vendors, high-energy music, and zero judgment. Come hungry, leave converted.
Chicago Pride Fest (Day 1)
Northalsted | All Day
Live music on multiple stages, drag excellence, and rainbow everything. Suggested donation: $20.
Juneteenth, the Great Migration & Bronzeville
June 21 | 11 a.m.–Noon | 70 E. Pershing Rd.
Historian Bernard Turner shares stories of migration and legacy.
West Pullman Juneteenth Festival
June 21 | 1 p.m.–6 p.m. | 821 W. 115th St.
Music, food from Black-owned restaurants, plus housing and small business workshops.
Juneteenth in the Burbs!
June 21 | 2 p.m.–6 p.m. | Harper College, 1200 W. Algonquin Rd., Palatine, IL
Live jazz, youth talent, poetry, and a Freedom Exhibit. Free books, food, and engagement with Black professionals. No cost to attend.
Navy Pier Fireworks
Pier Promenade | 10 p.m.
Free. Fabulous. Explosive. Find your spot and take it in.
Sunday, June 22
Soul Brunch: Tribute to Chicago Soul
City Winery | 12 p.m. (Doors at 11 a.m.)
From Curtis to Chaka, enjoy live soul classics while digging into a top-tier brunch spread.
Chicago Pride Fest (Day 2)
Northalsted | All Day
More music, drag, dancing, and celebration in one of Chicago’s most iconic queer neighborhoods.
Vegandale Festival – Day 2
Butler Field, Grant Park | All Day
If you missed day one, round two’s just as delicious.
Juneteenth Jamboree
Roots Handmade Pizza – South Loop | 3 p.m.–9 p.m.
No yacht? No problem. Celebrate Black joy with DJs, dancing, drinks, and unapologetic vibes. Ages 21+.
Monday, June 23
The Floacist (of Floetry) – Live
City Winery | 7 p.m. (Doors at 5:30 p.m.)
Grammy-nominated and soul-certified, The Floacist makes her solo U.S. debut—part spoken word, part celebration, all heart.
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