With the recent emergence of children expressing non-binary and nonconforming gender identity, parents across the United States have responded with confusion and concerns for their children (Havrilesky 2019; Moyer 2022). In the Hyde Park neighborhood of Chicago, Illinois, the number of children expressing non-binary and nonconforming gender identity has increased in recent years. This study of four parents in Hyde Park investigates to what extent they accept their children’s statements of gender identity as authentic and true, how they support their children within and beyond the dynamic family, and what concerns they have for their children as they navigate the world with these expressed gender identities. While parents had unique approaches to supporting their children, they all honored their children’s requests to use different pronouns and, in some cases, names. Parents acknowledged the resources specific to Hyde Park, including school policies, support groups and clubs, access to other parents and children exploring gender identity, overnight camps, and religious institutions, which have fostered an accepting environment for their children to be comfortable expressing their gender identities. Parent concerns were primarily focused on aging and the physical changes that come along with it, which may cause mismatch with gender identity, moving out of Hyde Park into environments where they may be judged or teased based on gender identity, and laws being passed in certain states against the discussion of gender and sexuality in schools and medical intervention for gender identity.