Rob Clearfield grew up in Oak Park, Illinois, a few miles west of Chicago, in a house full of music: his mother worked as a church music director and music teacher, and his own adolescence ran through garage bands, gospel choirs, and South American guitar ensembles before it settled on the piano. He moved into Chicago proper to study at the Chicago College of Performing Arts at Roosevelt University, where he worked with pianist Jim Trompeter, and he stayed in the city for fifteen years afterward, becoming one of the most heavily booked keyboard players on its modern jazz scene.

Two of his earliest long-running bands were not jazz groups at all. In the fall of 2006 he co-founded the progressive rock band District 97 with drummer Jonathan Schang, bassist Patrick Mulcahy, and guitarist Sam Krahn, playing keyboards on the band's Hybrid Child (2010), Trouble With Machines (2012), In Vaults (2015), and the live One More Red Night: Live in Chicago (2014), recorded with former King Crimson and Asia singer and bassist John Wetton. He left District 97 in August 2015. He was also a founding member of the Chicago indie band Hood Smoke, and he wrote all the music for Information Superhighway, his own quartet with vocalist Leslie Beukelman, Mulcahy on bass, and John Smillie on drums, which released the live 7/31/09 and the studio EP This is Not the Ending in 2010 and reconvened remotely in 2021 for the single "Learning How To Walk."

His jazz work ran alongside all of that from the start. He joined bassist and composer Matt Ulery's group Loom for Music Box Ballerina (2008) and stayed with Ulery's projects for roughly a decade, playing on Themes and Scenes (2009), Flora. Fauna. Fervor. (2011), the double album By A Little Light (2012, Greenleaf Music), Wake An Echo (2013), In The Ivory (2014), Festival (2016), and the analog-tape date Trio (2017). On By A Little Light he shares the piano chair with Ben Lewis, taking six of the album's twelve pieces. He also became a regular in groups led by saxophonist Greg Ward, vocalist Grazyna Auguscik, and drummer Makaya McCraven, both on stage and in the studio, and turns up on McCraven's In These Times (2022) alongside pianist Greg Spero.

He began his own leader catalog in 2009 with A Thousand Words, an entirely improvised solo record cut in a single October session on a Fazioli grand at PianoForte Studios in Chicago, and followed it with the 2/26/10 live document of its release concert, another wholly improvised performance in the same room. The Beauty That We Live In (2010), a five-song EP of sacred material, was made with vocalist Bethany Hamilton, who later became his wife. The Long and Short of It (2013) put him in front of a working quintet with tenor saxophonist Scott Burns, guitarist John Kregor, Patrick Mulcahy on bass and Eric Montzka on drums, and Islands (2016, ears&eyes Records) was his first trio album, with Curt Bley on bass and Quin Kirchner on drums. His second solo record, Wherever You're Starting From (Woolgathering Records, February 2018), assembled written pieces and edited improvisations into a twelve-track program that also holds a Johannes Brahms intermezzo and John Coltrane's "Giant Steps." Clearfield has said the album's material came out of conversations with McCraven about building finished compositions from improvised fragments.

In 2019 he and saxophonist Caroline Davis released Anthems on Sunnyside under the name Persona, a co-led quartet with Sam Weber on bass and Jay Sawyer on drums, named for the Ingmar Bergman film and recorded in Brooklyn in February 2018; a live duo set from the California Jazz Conservatory followed as Anthems Live. That same year Clearfield left Chicago for France, and he now lives in Marseille. His work since has split between free duo playing and long-form composition: Concentric Orbits (2022, Astral Spirits) is a thirty-minute piano and drums improvisation with Quin Kirchner, captured in one Chicago session in September 2019, while Ashes and Diamonds (2023, ears&eyes) is a five-movement suite for quartet with Greg Ward on alto saxophone, Sam Weber and Kirchner, written around how upheavals push one era into the next. Voice in the Wilderness (Jazz&People, May 2025) is his first record made in Europe, a trio with double bassist Joe Sanders and drummer Fred Pasqua, with two tracks produced by McCraven.

His association with Israeli trumpeter Itamar Borochov runs across three records and seven years. Clearfield holds the piano chair on Borochov's Blue Nights (2018, Laborie Records), a quartet date with the trumpeter's older brother Avri Borochov on double bass and oud and Jay Sawyer on drums, and he plays piano, Rhodes and B3 organ across Arba (2023, Greenleaf Music), cut over two days in April 2022 at Big Orange Sheep in Brooklyn with Rick Rosato on bass and Jay Sawyer on drums, produced by Matt Pierson with Dave Douglas as executive producer. He toured in Borochov's quartet, appearing with him in Oslo in February 2023, and Borochov returns the favor on Voice in the Wilderness, playing trumpet on four of its nine tracks. Away from the bandstand, Clearfield has written on commission for the Brazos Valley Symphony Orchestra in College Station, Texas, for theater at Purdue University, and for the film The Lost Remake of Beau-Geste, and he teaches piano at the Stanford Jazz Workshop.

Clearfield's piano writing sits deliberately between jazz and European concert music, and critics have reached repeatedly for the same vocabulary to describe it. Peter Margasak, writing in the Chicago Reader about Wherever You're Starting From, called it a "feathery jazz-classical hybrid" and noted that Clearfield's phrasing is so saturated with classical language that his reading of a Brahms intermezzo sounds like one of his own pieces, while his "Giant Steps" comes out as a rhapsodic fantasia rather than a bebop exercise; Margasak heard romanticism, impressionism, and the influence of Bill Evans and Keith Jarrett running through the originals. The Chicago Tribune's Howard Reich described his music as arriving "as a kind of balm" in a noisy world. He is equally a group player who disappears into an arrangement, which is why he has been the harmonic anchor of so many other people's records: Matt Ulery's chamber-jazz ensembles, Greg Ward's concerto for jazz quartet and string orchestra, Makaya McCraven's assembled studio pieces. He is unusual in the range of keyboards he brings to those settings, moving between acoustic piano, Rhodes, Wurlitzer, Moog, Hammond B3 and pump organ, and he plays guitar and accordion on record as well. His first three albums as a leader were built from pure improvisation, and the compositional turn that produced Ashes and Diamonds grew out of an editing approach he developed with McCraven, cutting long improvisations down to the material that could carry a written form.