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Live music in Chicago this weekend, Fri, Jun 26 – Sun, Jun 28. 500+ shows across Chicago, the suburbs, and NW Indiana.

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Friday, June 26221 shows

City WineryWest Loop
Jamal Roberts - Perfect for Me Tour
7:30pm

Jamal Roberts - Perfect for Me Tour

Born November 6, 1997 in Meridian, Mississippi, Jamal Roberts is the breakout soul artist of 2025. After winning Season 23 of American Idol with a record setting 26 million votes, the highest since the show’s move to ABC Hulu, Jamal has swiftly transitioned from a fan favorite to a chart topping artist. His debut single, “Heal,” a stirring reinterpretation of Tom Odell’s ballad infused with gospel and R&B elements, debuted at No. 1 on both the Billboard Hot Gospel Songs and Gospel Digital Song Sales charts. The track also secured a spot in the top 10 on the Gospel Streaming Songs chart, marking a significant milestone for a debut release. “Heal” has been featured on prominent playlists across major streaming platforms, including Apple Music’s “New Music Daily” and Spotify’s “Fresh Gospel & R&B,” amplifying its reach and resonating with a diverse audience. Building on the momentum, Jamal will exclusively selected to tour with Brandy & Monica on their highly anticipated The Boy Is Mine tour Jamal’s performances have garnered millions of views on YouTube, millions of streams, rendered him as the headliner for The College Football Playoffs National Championship, & even a 2026 Grammy Nomination. Jamal Roberts is not just an artist to watch, he’s a voice that defines a generation.

from $30

MetroLakeview
Old Gold
9:00pm

Super Sapphic V

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All-Building sapphic event with DJs and performances

Today · Saturday, June 27199 shows

Chopin TheatreWicker Park
Lisa Kaplan
2:00pm

In Perpetual Motion

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Music from Lisa Kaplan's debut album, and the premier of To Whom Do We Belong created in collaboration with acclaimed puppeteer, Blair Thomas.

$20

City WineryWest Loop
Anime & Wine Brunch
12:00pm

Anime & Wine Brunch

City Winery Chicago Presents Anime & Wine Brunch live on Saturday, June 27th! Join us for an elevated anime experience at City Winery for a day party of wine, trivia, games, anime and community in Chicago. With an eclectic mix of city pop and Japanese R&B thematically paired with anime for a visual, sonic and tasting experience. Includes 1 welcome amuse glass of wine!

from $21.6

Tomorrow · Sunday, June 2880 shows

City WineryWest Loop
Rosé & Resilience: An Evening of Wine, Talent & Expression
7:00pm

Rosé & Resilience: An Evening of Wine, Talent & Expression

City Winery Chicago Presents Rosé & Resilience: An Evening of Wine, Talent & Expression live on Sunday, June 28th at 7:00 PM! Join us for Rosé & Resilience, a celebration of PRIDE. Thanks to the "Cheers to Love" campaign, we have another opportunity to celebrate in an immersive cultural experience that redefines the traditional performance showcase. Hosted at City Winery Chicago, this elevated evening blends sensory delight with powerful storytelling to center LGBTQ+ visibility, community, and celebration. Rather than a standard show, the night functions as a living artistic tapestry. Guests will experience a sophisticated, soulful atmosphere where fine wine meets dynamic expression. The Evening Features:

from $30