Chicago-based Indie-folk singer-songwriter Chris Rawlins is set to release his much anticipated sophomore album, Flyover, on October 24, 2025 — a spacious, haunting, and deeply personal exploration of place, memory, and the quiet emotional weather systems of adulthood. The album arrives six years after Rawlins' critically-acclaimed 2019 debut Bring on the Rain, and stands as both a sonic evolution and a return home, in more ways than one.

Described by Rawlins as “a love letter to the landscapes, culture, and mystique of the Midwest,” Flyover meditates on the region’s overlooked beauty and unique emotional terrain. Through richly imagistic lyrics and immersive, Terry Allen-esque folk instrumentation, Rawlins paints a world of cornfields that become desolate oceans at dusk, of shadowy cities, and of love lost to a dreamlike longing — all filtered through the lens of a songwriter quietly observing from 30,000 feet above, and decades removed from childhood.

The album’s first single, “After Dark,” will be released on September 12, followed by “Break Even” on October 3, ahead of the full album drop. Both tracks exemplify the album’s central themes — introspection, wistfulness, and the peculiar dislocation of life in a region often written off as “flyover country.”

“I started with the idea of ‘flyover’ as a concept" Rawlins says, “but it grew into something more emotional. It’s not just the Midwest being flown over — it’s about people being passed over, forgotten, left behind. There’s a quiet ache to that. And I think a lot of folks have felt it, especially in the past few years.”

The concept of Flyover has roots going back as far as 2019, when some of the earliest songs were written, even before Rawlins released his debut. But the recording process, stretched across several years and interrupted by the COVID-19 pandemic, didn’t officially take shape until 2022 — when Rawlins began recording sessions with producer and engineer John Abbey (Robbie Fulks, John Cale) at Kingsize Sound Labs in Chicago.

What emerged is a cohesive, atmospheric album that Rawlins and Abbey carefully shaped with a sense of visual and sonic intentionality. Many of the songs — including “After Dark” and “Like a Bird, Like a Sound” — began not as narratives, but as attempts to musically describe photographs. The most central of these is the album’s striking cover image, an aerial photograph taken in 1983 over Berrien County, Michigan by Rawlins’ father, photographer Gary Cialdella.

“That image has been in my life for a long time,” Rawlins explains. “I kept it in mind throughout the writing and recording. It felt like the landscape I was writing about — vast, moody, mysterious. I wanted the album to feel like that photo sounds.”

The result is an album that blends fingerpicked folk with ambient textures, reverb-laden electric guitar, and organic instrumentation — creating a spaciousness that allows the lyrics to breathe. Rawlins’ vocal performances remain intimate and tender, delivered with the kind of emotional clarity and restraint that marks the best of modern indie-folk. Contributors include Gerald Dowd and David Prusina on drums, Matthew Pittman and John Abbey on electric guitar, and Brian Wilkie on pedal steel.

Tracks like “You Were Young” and “Break Even” explore the bittersweet process of aging and self-doubt through a distinctly Midwestern lens. “Break Even” was written intentionally to reflect that feeling of coming up short — of being close, but never quite there. Rawlins explains: “It’s that ‘cool by association’ vibe — like you’re rubbing elbows with greatness but still a step behind. That’s a very Midwest feeling, I think.”

“Firefly”, written after a visit to Oregon where Rawlins’ nieces marveled at the thought of the Midwestern insects they’d never seen before, uses the glowing creatures as a metaphor for the fleeting nature of time and youth. “It hit me that something I took for granted growing up was actually unique to this place,” he says. “And that seemed to say something about identity and change.”

Throughout Flyover, Rawlins moves seamlessly between memory and metaphor, grounded in geography but untethered from strict chronology. “You Were Young”, the oldest song on the album, was originally written for his debut but shelved — only to be rediscovered years later with renewed resonance. “I wrote it when I was in my twenties, imagining what aging might feel like,” he recalls. “Now I’m actually approaching middle age, and it hits totally differently. It’s like writing a letter to your future self, then finally getting to read it.”

Originally from Kalamazoo, Michigan, Rawlins’ musical path led him briefly through the fabled folk clubs of New York City before he ultimately settled in Chicago in 2014, where he found both inspiration and community.

“Chicago felt honest in a way New York didn’t,” he says. “I could pay rent and make music. I found people who cared more about the work than the image. That’s where this record really took root.”

Flyover is Rawlins’ most cohesive and conceptual work to date — a quiet, widescreen collection that speaks to anyone who has ever felt out of place, nostalgic for home, or suspended between what was and what might have been.

Flyover – Tracklist:

1. After Dark
2. You Were Young
3. Like a Bird, Like a Sound
4. Firefly
5. Break Even
6. More Perfect
7. Flyover
8. Nondescript
9. Anywhere

Credits:

All songs written by Chris Rawlins (ASCAP) | Published by Side Salad Music (ASCAP)
Produced by Chris Rawlins & John Abbey | Recorded at Kingsize Sound Labs (Chicago, IL)
Mastered by Scott Anthony at Storybook Sound (Maplewood, NJ)
Cover photo: Plowed Fields, Berrien County, 1983 by Gary Cialdella

For fans of: Gregory Alan Isakov, Jackson C. Frank, Devendra Banhart, Jim Croce, Gillian Welch

For press inquiries, interviews, or review copies, contact:
Benji Michaels: benji@dogranchmusicpr.com
Ron Kadish: ron@dogranchmusicpr.com