Lollapalooza Chicago is throwing another four-day rager in Grant Park, and once again, the lineup is massive. Between the usual pop giants, gritty rock, and dance-floor chaos, there’s a lot to sort through. But we’ve been keeping tabs. Whether you’re pulling up for the first time or you’re a seasoned wristband veteran, here are the artists we can’t stop thinking about — and why you should care too.

Olivia Rodrigo
She’s still in her early twenties, but Olivia Rodrigo already has a generation in her grip. Guts proved she wasn’t a one-album wonder, leaning deeper into snarling guitar riffs and gut-punch lyrics. She’s toured the world, played the biggest stages, and hasn’t slowed down. Word is, new music is coming before summer’s out, and you can bet she’ll test a few of those tracks on the Lolla crowd.
Olivia’s shows are part confessional, part riot. Fans scream every word like it’s gospel. She’s emotional, unpredictable, and always in control. If you’re anywhere near her set and you hear the first notes of “vampire,” get ready to be swallowed by the sound of 100,000 hearts breaking at once.

Tyler, The Creator
Tyler live is a whole different beast. He doesn’t just run through a setlist, he creates his own world. Whether he’s performing in a pastel suit or climbing up set pieces mid-song, there’s always something to watch. His last record, Chromakopia, added even more layers to his catalog. It’s raw, full of flexes, and more reflective than ever.
He’s not dropping new music this year that we know of, but it honestly doesn’t matter. His shows are tight, his banter’s sharp, and his energy’s unmatched. You don’t want to miss him.

Twice
If you’ve never seen a K-pop group live, Twice is a great first. They’ve been in the game for nearly a decade and still move like they’re chasing their debut. Every routine is flawless, every outfit change on cue, and the vocals are live, polished, and powerful. They’ve become global superstars without losing their charm.
Their latest album Dive feels like a love letter to fans, and their newer material has taken a more mature turn. Expect dance anthems, glowing fan chants, and a synchronized wall of sound that’ll give you goosebumps.

Cage The Elephant
It’s been six long years since Social Cues, and they finally dropped Neon Pill last year. It’s weird, groovy, and as unhinged as you’d expect. Frontman Matt Shultz is back after a rough patch, and you can feel that rawness in their latest work.
Their live sets are electric. Shirtless chaos, guitars getting chucked, and the whole band running on some beautiful mix of anxiety and adrenaline. This is the kind of show you stumble into and walk out a fan. Don’t sleep on them.

Doechii
2025 is Doecchi’s year. There’s no one quite like her. She flips between rap, R&B, and electronic sounds without breaking a sweat. She’ll hit you with rapid-fire bars one minute, then drop into a melodic hook the next. Her performances are part performance art, part dance battle, and all attitude.
She released her album Alligator Bites Never Heal last summer, and she’s only getting louder. If you want to catch an artist right before she blows up even bigger, this is your window.

The Marías
Chill, dreamy, and a little seductive, The Marías bring a mood. Their 2024 release, Submarine, took their psych-pop roots and gave them a pulse. They’ve added more movement to their sound without losing the hazy magic that made them stand out in the first place.
If you’ve seen them opening for Billie Eilish on her lastest tour, you know their set will be a palette cleanser. Grab a drink, sway a little, and let frontwoman María Zardoya’s voice wash over you. Pure sunset-core.

Remi Wolf
Remi’s not interested in staying in one lane. Her latest tracks pull from funk, alt-pop, and a little punk chaos. It’s messy in a good way. Her lyrics are weird and wonderful, and her delivery feels like she’s fighting off a giggle half the time.
Live, she’s a total firecracker. No backing track safety net, just full-force vocals and a whole lot of cardio. Her shows are colorful, sweaty, and deeply fun. You won’t walk away bored.

Ravyn Lenae
Chicago’s own Ravyn Lenae is coming home, and her set is going to be special. Her debut album Hypnos was a stunner with slick production, buttery vocals, and a vibe that feels like neon lights reflecting off wet pavement. Since the, she’s dropped her second album Birds’ Eye.
Her performance style is smooth, but never sleepy. It’s R&B that knows how to move. If you want to slow it down without tuning out, find your way to her stage.

Magdalena Bay
This duo feels like the future of synth-pop. Their visuals are glitchy, internet-core weird, and completely hypnotic. Their album Mercurial World still holds up, and the follow-up Imaginal Disk is even stranger. Perfect.
They’re a full-package kind of act. The music slaps, the projections are trippy, and there’s this wink to everything they do. It’s art school meets dance party. If you like your pop smart and a little spooky, don’t skip them.

Role Model
Tucker Pillsbury, aka Role Model, makes sad-boy pop that cuts deeper than you’d think. His new stuff leans darker, with more texture and less polish. There’s growth here, both lyrically and musically, but he’s kept that sense of intimacy that made fans fall for him in the first place.
Live, he brings just the right amount of mess. Emotional but not melodramatic. The kind of performance that sticks with you after you leave the crowd.

There’s no way to catch everything, but if you hit even half of these sets, you’re in for a good time. The headliners will bring the flash, sure, but the real moments will be found in the in-between. Keep your ears open and your schedule loose. Lollapalooza 2025’s full of surprises.

Visit Lollapalooza’s website for all the details!