The Ravinia Festival isn’t your typical concert venue and Saturday night wasn’t your typical show.

As thousands gathered in Highland Park, just outside of Chicago, with picnic baskets, bottles of rosé, and rainbow flags in hand, the second major concert of Ravinia’s 2025 season transformed the scenic, tree-lined amphitheater into a sanctuary of sound, style, and self-expression. The pairing of two genre-bending icons, Grace Jones and Janelle Monáe, was a once-in-a-lifetime experience that felt tailor made for Pride Month. It was futuristic. It was funky. It was fearless.

Janelle Monáe: Opening with Headliner Energy

Janelle Monáe might have technically opened the night, but her performance was anything but secondary. The acclaimed artist brought her unmistakable blend of Afrofuturism, soul, and pop polish to Ravinia’s stage with commanding presence, igniting the crowd from the jump. With hits like “Make Me Feel” and selections from her Age of Pleasure era, Monáe blurred the lines between concert and theatrical production, dripping charisma and reminding everyone that she can, and does, headline festivals on her own.

Monáe’s performance also echoed the spirit of Pride in both message and aesthetic. Between songs, she shared messages of empowerment and visibility, championing queer joy in a world that too often stifles it. She made Ravinia’s lawn feel less like a north shore park and more like a utopian block party, with concertgoers dancing in the grass, glitter on their cheeks.

Grace Jones: The Queen Ascends (Literally)

Then came Grace Jones.

As the curtain fell, the stage revealed Jones poised atop a towering platform, wearing a striking red mask that looked like a cyberpunk welder’s helmet. It was theatrical, menacing, iconic. She opened with her take of Iggy Pop’s “Nightclubbing,” her voice slinking through the air like velvet smoke, and from that moment on, the audience was hers.

At 77, Grace Jones remains a marvel. Her set was part fashion show, part performance art, part dance party, and all Grace. The hits came one after the other: “Demolition Man” and the sly groove of “My Jamaican Guy” drew roars from both the pavilion and the packed lawn. Lawngoers, some listening from their blankets on the ground, others sipping cocktails from crystal glasses, were just as locked in as those with front-row seats.

She commanded the stage with magnetic eccentricity, balancing avant-garde visuals with raw musical power. During “Williams’ Blood,” she delivered vocals that were chilling in their intensity. Her take on “Amazing Grace” was stirring and oddly intimate, even in a venue filled with thousands.

But the night’s true climax came during “Pull Up to the Bumper,” when Monáe reappeared to join Jones on stage. It was a generational summit of two trailblazers, exuding mutual respect, joy, and defiance. Finally, “Slave to the Rhythm” closed the night in spectacular fashion, although the crowd certainly didn’t want it to end.

Ravinia’s Unique Magic

There’s truly nowhere else like Ravinia. While many venues are content with plastic chairs and overpriced beer, Ravinia invites fans to build their own experience. Couples on the lawn dined by candlelight, groups of friends lounged on picnic blankets decked out like living rooms, and families danced among hanging string lights and garden gnomes.

That sense of personal celebration blended perfectly with the ethos of the night: be yourself, love freely, live loudly.

Grace Jones and Janelle Monáe gave Pride Month a North Shore moment it won’t soon forget.

Check out photos from Saturday night’s unforgettable performances below (Photo by Dan Garcia/The Early Registration).