Joey and Mary Alice change quite a bit during the six summers they spend with their grandmother. Both individually and as a unit, the siblings discover who they are and who they want to be, gaining help from both internal and external sources. By following their character arcs across the multiple stories in A Long Way From Chicago, the book explores the myriad ways in which children find their own paths to adulthood.

As individuals, Joey and Mary Alice paradoxically grow both apart from each other and closer together as the summers pass. In the early chapters, the siblings spend time together at Grandma’s house simply because there is little else for them to do. While spending time together may not be their first choice, the situation is tolerable, and whether they realize it or not, being around each other helps them both to grow. In Chapter 7 when Grandma and Mary Alice insist on joining Joey for his driving lesson, Joey doesn’t want them there because “learning to drive was kind of a sacred thing, and you don’t want your kid sister and your grandma along” (118). Despite this initial aversion to his family’s presence, the lesson goes well, and Joey is still able to grow as an individual, even with his family in attendance.