Hometown Heroes: Chicago Acts Representing at Lolla 2025

Every year, Lollapalooza turns Grant Park into a musical playground — and while the global stars bring the headlines, it’s the hometown talent that gives the festival its soul. In 2025, Chicago’s local artists aren’t just filling out the schedule. They’re stepping into well-earned moments, carrying the city’s legacy of innovation, resistance, and reinvention into a new era.

Chicago’s music scene has always been a shape-shifter. From house to drill, indie rock to footwork, the city births entire genres and movements without ever asking for permission. This year’s Lolla lineup features a new generation of local artists who are carrying that spirit forward — blending styles, challenging expectations, and bringing all the grit, heart, and magic that makes Chicago one of the most influential music cities in the world.

Ric Wilson

If you’ve never danced your ass off while also having your mind blown, you’ve never seen Ric Wilson live. The Chicago-born rapper, funk enthusiast, and self-proclaimed “disco poet” is known for turning his sets into joy-filled protests and party-like political rallies. His music blends funk, hip-hop, and soul with radical optimism — and it slaps. Come for the beats, stay for the message (and maybe a little two-step).

Sen Morimoto

A multi-instrumentalist, singer, rapper, and producer, Sen Morimoto does it all. His sound defies genre: jazzy, synthy, sometimes rapped, sometimes sung, always rich with texture. Originally from Japan but now deeply embedded in Chicago’s DIY and indie scenes, Sen is the type of artist who can go from a whisper to a wail in one breath. Expect a cerebral yet soulful set that showcases Chicago’s weirder, artsier corners.

KAINA

KAINA is what happens when you blend Chicago soul with Latinx storytelling and a warm, honeyed voice. Her music radiates comfort — intimate, honest, and full of gentle defiance. As a proud first-gen Latina and longtime collaborator within the local scene, her presence at Lolla is a celebration of culture, community, and vulnerability as strength.

These artists aren’t just repping Chicago — they are Chicago. Whether they’re playing mid-day slots or opening a stage, they carry the stories of neighborhoods, cultures, and communities that rarely get amplified at mainstream fests. Catch them before their stages overflow. Because once that crowd sees what Chicago already knows? There’s no going back.

photo by Dennis Elliott