This is a qualitative systematic review of recent qualitative studies of the experiences and perceptions of both individuals with chronic illness(es) and their caregivers regarding hospital-to-home transitions. Thematic synthesis was used to identify common themes from seven qualitative studies published from 2012 to 2021 and extracted from four electronic databases. This review was guided by the Preferred Reporting Items for Systematic Reviews and Meta-Analyses Statement. Quality appraisal was assessed and adequate methodological rigor was determined. A total of three barriers to transitional care (communication with multiple healthcare providers, self-management, and psychological stress) and two facilitators of transitional care (family caregiver support and nurse-provided patient-centered care) were identified. These findings can be used by nursing research and healthcare managers to reform transitional care practices for chronic illnesses and caregivers.