Ryley Walker
Friday, 3:30 PM, Blue Stage
This spring Ryley Walker released his best and most mature record, Primrose Green (Dead Oceans), produced by Cooper Crain of Bitchin Bajas (see below). But as rich and nuanced as the album is, it can’t compete with what this Rockford transplant does onstage. Though he’s still playing a stretched-out version of the title track, a recent full-band set in New York consisted mostly of new material, and the improvisational rapport between lead guitarist Brian Sulpizio and keyboardist Ben Boye was in full bloom. Walker continues to grow as a singer, but where he and his comrades really excel is in bringing quicksilver spontaneity to his dreamy folk-rock meditations. —Peter Margasak
Wilco
Friday, 8:30 PM, Green Stage
Pitchfork was one of the first to deride Wilco as “dad rock” (in a 2007 review of Sky Blue Sky), so it’s almost funny to see the band appear as a headliner this year. Maybe some of Pitchfork’s staff have become parents, or maybe they’ve realized what a moronic thing that was to call a group that draws widely from rock history but favors craft over aggression or petulance. Pitchfork champions plenty of acts that follow that MO, and Wilco easily outdo almost all of them—they transform the past exceptionally well, bolstered by a great songwriter and one of the most talented groups of musicians active in the past decade or so. —Peter Margasak
Jimmy Whispers
Saturday, 1 PM, Green Stage
For most of the past few years, the only way to hear the sick-to-your-stomach-sweet love songs of lo-fi pop auteur Jimmy Whispers was at one of his unhinged, unpredictable live shows—but this spring Moniker Records released his long-in-the-works first album, Summer in Pain. Its earnest, vigorous tunes plant their flag in your brain: for what feels like ages I’ve been singing bits of the intoxicating, wistful “Heart Don’t Know” to myself. Jimmy performs with heart and intensity—it’s clear he desperately needs to let something out that’s been building up inside him—and in concert he doesn’t hesitate to help potential fans embrace his music by getting right in their faces. His new six-piece backing band should help him spread that enthusiasm. —Leor Galil
Vic Mensa
Saturday, 8:45 PM, Blue Stage
Vic Mensa’s full-length debut, the breezy, beautifully soulful 2013 mixtape Innanetape, would’ve been a great way for him to make a first impression—if it’d actually been a first impression. But Mensa, now 22, cut his teeth in hybrid rock group Kids These Days, which broke up shortly before he released Innanetape, and when he was 14 he cofounded Chicago hip-hop collective Save Money—alongside Chance the Rapper, whose runaway success has pushed him to follow suit. Mensa is coming into his own: he recently signed with Roc Nation, and he’s collaborated with Kanye West on several tracks, including this spring’s massive-sounding “U Mad.” My favorite Vic Mensa cut remains the sleek, house-inflected 2014 single “Down on My Luck”; he rhymes like a kid sliding across a freshly waxed floor in his socks—and even when you think he’s overdue to pause for breath, he’s got a few more butter-smooth lines left in him. —Leor Galil
Bitchin Bajas
Sunday, 1 PM, Green Stage
Bitchin Bajas (the trio of Cooper Crain from Cave, Rob Frye, and Dan Quinlivan) have developed and finessed their sound in the past couple years, transforming themselves from hypnotic Krautrockers into kosmische wizards with a collective Terry Riley obsession. On their recent EP, Transporteur (Hands in the Dark), synth arpeggios cycle feverishly, their microscopic mutations changing the shape of each piece subtly but decisively, while Frye blows weightless, spell-casting flute lines. The trio isn’t averse to beats, though, and “No Tabac” incorporates rolling syncopations that seem to anticipate a forthcoming collaboration with Joshua Abrams’s Natural Information Society, due this summer on Drag City. —Peter Margasak
How to Dress Well
Sunday, 4:45 PM, Blue Stage
The alt-pop wonderlands that Tom Krell creates as How to Dress Well don’t sound like they belong to Chicago. You could file his most recent album, last year’s What Is This Heart? (Weird World), next to records by LA beatsmiths Baths and Active Child—all three pair frantic beats with clingy hooks and frequent falsetto vocals. But Chicago is the city How to Dress Well calls home, at least when Krell isn’t on tour or living in Berlin, where he wrote much of Heart. Backed by a full band, Krell puts on a show for a stadium no matter what venue he’s in—though he’s playing the smaller Blue Stage, you’ll be able to hear him croon from every corner of the park. —Sasha Geffen
Chance the Rapper
Sunday, 8:30 PM, Green Stage
Wunderkind MC Chance the Rapper has gone global since his 2013 breakout mixtape, Acid Rap, in the process solidifying the lineup of the Social Experiment, his vivacious live band. Though this headlining set belongs to Chance in name, for part of it he’ll likely hand over the reins to Nico Segal, aka Donnie Trumpet of the Social Experiment. Segal was the de facto leader on the band’s recent free album, Surf, whose summery, happy-go-lucky pop gleams with his fluid horn playing. Taken as a whole, Surf feels like the soundtrack of a Broadway musical, which can challenge the patience of less charitable listeners—fortunately, many of its individual tracks stand on their own just fine. Chance’s contributions are killer, and sometimes it sounds like all of Chicago is joining in to sing along. —Leor Galil v