MacKay was born in Tarrytown, New York on April 3, 1968. He grew up in Rochester, New York and Pittsburgh, Pennsylvania, the son of a trumpeter (both parents were fans of Broadway show tunes, classical music, and jazz). His early influences include the Beatles, Frédéric Chopin, John and Alice Coltrane, Jimi Hendrix, and Laura Nyro, among others, and his literary influences include beat poets Kenneth Patchen and Jack Kerouac, Edgar Allan Poe, and Antonin Artaud. In Rochester, he briefly studied classical guitar with Kevin Morse, and in Pittsburgh he was in the music program at Chartiers Valley High School from 1982-1984 and Penn Hills High School, graduating in 1986, taking further instruction with guitarists Eric Susoeff and Joe Negri. MacKay attended the Berklee College of Music in Boston for the next two years and took a course in improvisation and composition with pianist, violinist, composer, and singer Alice Orpheus at the New England Conservatory in 2005.
Shortly after arriving in Chicago he networked across several musical communities. In 2005, he contributed to vanguard jazz violinist SavoirFaire's Running Out of Time on Delmark. The same year, Bill Mackay Sounds of Now was issued by Sons of Fire. Broken Things made its recorded debut in 2007 with the wildly eclectic album Swim to the River, a set that wove soundtrack-style sounds with hard rock and modal and free jazz. It proved a busy year as MacKay also played with Colorlist on their debut Lists, and with bassist Jason Ajemian's unit Who Cares How Long You Sink's debut offering Folk Forms Evaporate Big Sky. In 2010, MacKay was an integral part of the band that brought late songwriter Paul Mooney's Because of a Woman to fruition. The songwriter/poet who fought a life-long battle with cystic fibrosis had recorded vocal and guitar tracks with the hope of completing an album. He died after finishing six songs. His brothers enlisted MacKay, Dorian Taj, and Ronda Duvall to complete them. The same year, Bill MacKay and Darts Arrows released their eponymous debut. The band included Matthew Golombisky on bass, Ben Boye on keyboards, and Charles Rumback on drums. Greg Ward contributed clarinet to the set's most poignant tune, "Black Leaves."
The next few years were full of frenzied activity. In 2011, he was a recording member of jazz bassist Marc Plane's Walk East on its self-titled debut. Darts Arrows dropped MacKay's name from its moniker and released the full-length Eyes of the Carnival in 2012. Two years later, the guitarist issued two of his own albums, December Concert, in duet with guitarist Matt Lux, and Chatham Park, as well as contributing to a pair of albums by singer/songwriter Angela James. The following year he issued another duet set with Ryley Walker titled Land of Plenty. Darts Arrows issued its third offering, the acclaimed Altamira. MacKay also played on The Gravity of Our Commitment by the large vanguard jazz ensemble Never Enough Hope, a unit that plays compositions by Toby Summerfield. To round out 2015, Tompkins Square issued the solo acoustic set Sunrise: Bill Mackay Plays the Songs of John Hulburt.
In 2016, MacKay was an ensemble member of Rob Frye's (Cave/Bitchin Bajas) Flux Bikes/Sueñolas for its limited-cassette issue of the same name. MacKay signed to Drag City in early 2017, and his debut album Esker was released in May. He described its contents as "spirit guitar played in a polyglot of styles that melt together liquidly, like the glass slide figurations throughout the album. A landscape in song, and modern guitar on a personal high." The following year he and frequent touring partner Ryley Walker issued SpiderBeetleBee, a collection of guitar duets described as "slide blues, Baroque dance, percolating Latin, and deep-focus space" tunes on Drag City. Influenced by the more intimate view of and approach to recording on Esker, MacKay recorded completely solo for 2019's acoustic Fountain Fire, playing all the instruments ranging from guitars and requinto to organ, percussion, and piano. Later in 2019, MacKay brought out the album STIR, a collaboration with Katinka Kleijn, a cellist and artist who performs in classical, improvisational, and experimental rock ensembles. That same year, MacKay released a solo electric guitar piece, Scarf, in a limited edition of 50 cassettes; Drag City gave it a digital reissue in 2020. MacKay collaborated with multi-instrumentalist Nathan Bowles for 2021's Keys, an experiment in folk and roots music disciplines. ~ Michael G. Nastos, Rovi