Discussion Questions for Dear America: The Diary of Pringle Rose, Down the Rabbit Hole, Chicago, Illinois, 1871 by Susan Campbell Bartoletti

About the Book

Newbery Honor author Susan Campbell Bartoletti brings the story of a young girl caught up in a web of murder, lies, and the Great Fire of Chicago to bold life.

In the spring of 1871, fourteen-year-old Pringle Rose learns that her parents have been killed in a terrible carriage accident. After her uncle Edward and his awful wife, Adeline, move into the Pringle family's home — making life for her and her younger brother, Gideon, unbearable — Pringle runs away with Gideon to Chicago, seeking refuge from the tragedy, and hoping to start a new life. She becomes a nanny for the children of a labor activist, and quickly finds herself caught up in a web of intrigue and lies. Then, when a familiar figure from home arrives, Pringle begins to piece together the devastating mystery of what happened to her parents, and realizes just how deadly the truth might be. But soon, one of the greatest disasters this country has ever known, the Great Fire of Chicago, flares up, and Pringle is on the run for her life.

Discussion Questions

1. Why do you think Pringle writes her story in a diary? Do you already or would you like to keep a diary? Why or why not?
2. Do you think Pringle made the right choice by not returning to boarding school after the death of her parents? How would things be different if she had gone back to school?
3. Pringle takes one book, Alice’s Adventures in Wonderland, on her journey. Pretend you’re going on a trip and choose one book to bring. Why is this book special to you?
4. Ms. Ringwald’s beliefs are so embarrassing to her family that they commit her to a mental institution. Are her ideas and beliefs still considered radical today?
5. In 1871, Pringle and Gideon face many issues. Discuss the challenges that children with special needs face.
6. Why do Mrs. Duggan and her daughter-in-law treat Gwen badly on the train? Why do they treat her differently once they arrive in Chicago?
7. Which side of the labor union issue does Pringle agree with in the beginning of the book? Does she feel the same way throughout the book?
8. Why do you think Cager initiated the friendship with Pringle?
9. Do you think many fourteen-year-olds could be as brave and strong as Pringle? Why or why not?
10. Do you think a fire like the Great Fire of Chicago could happen today? Why or why not?