Drew’s great-uncle, characterized by his confident and mischievous nature, who temporarily trades lives with Drew and faces challenges from early 20th-century life.

Andrew’s playful and spirited older sister who helps Drew adjust to his new life by teaching him skills like playing marbles and offering her support.

The rambunctious younger brother of Andrew and Hannah, who admires Andrew and expects Drew to display similar masculine traits.

The story's antagonist, first encountered as an ornery old man in the present and later as a bullying cousin in the past, who challenges Drew in perilous situations.

Drew’s caring and empathetic aunt who manages household responsibilities while providing support and understanding for Drew’s situation.

Andrew's authoritative father who upholds the expectations of his time through strict discipline but shows underlying warmth towards the boys.

Andrew’s kind and attentive mother who cares for Drew during his stay in the past, protecting him and showing concern for his well-being.

The bully from Drew’s life in Chicago, whose tactics resemble those of Edward, indirectly helping Drew gain confidence through his experiences.