His wife was Jessie O’Kelly. At the time of his death in 1945, his residence was 108 South Roberson Street in Chapel Hill.
In 1923, his tailoring business was located in the space previously occupied by Gooch's restaurant. In 1924, the building burned, so he relocated to Graham Street. That location also burned down, so he moved to West Franklin Street by the late 1930s. O'Kelly and two other business partners opened the Standard Theater on West Franklin Street in 1924.
Besides owning and operating his tailoring business, O'Kelly was also a real estate developer and local enterpreneur.
He is buried in the Old Chapel Hill Cemetery.