Transgender and gender diverse (TGD) youth experience health disparities due to stigma and victimization. Gender-affirming healthcare mitigates these challenges; yet, we have limited understanding of TGD youth's healthcare experiences in the U.S. Midwest and South. Using a multiple case study design, we aimed to develop an in-depth and cross-contextual understanding of TGD youth healthcare experiences in one Midwestern state. Families with a TGD child under 18 were recruited with the goal of cross-case diversity by child age, gender, race, and/or region of the state; we obtained diversity in child age and region only. Four white families with TGD boys or non-binary youth (4-16) in rural, suburban, and small towns participated in interviews and observations for one year; public data were collected from each family's community. Thematic analysis was used within and across cases to develop both family-level understanding and identify themes across families. Findings include a summary of each family as it relates to their child's TGD healthcare experiences as well as the themes identified across cases: accessibility and affirming care. Although limited by a small sample with lack of gender and race diversity, this study contributes to our understanding of TGD youth healthcare in understudied regions.