Chicago Typewriter follows the intertwined lives of three individuals who lived during the 1930s Japanese occupation of Korea and are reincarnated in the present day. Han Se-joo is a famous, cynical bestselling author suffering from a severe case of writer's block, while Jeon Seol is a former veterinarian and a devoted fan who becomes his anti-fan. Their lives collide with Yoo Jin-oh, a mysterious ghostwriter who hides a dark secret behind his charming demeanor. As the trio navigates the complexities of their modern-day lives, fragmented memories of their past lives begin to surface. They must confront the unresolved traumas, political betrayals, and deep-seated loyalties of their previous incarnations to understand their current destinies. The series masterfully blends historical drama with contemporary mystery, exploring themes of fate, artistic integrity, and the enduring power of memory.