In mid-May, Sandy receives a letter from Annjee. Tempy has told her that Sandy has been staying out late, and since Annjee has had no word from Jimboy for seven months, she wants Sandy to come to stay with her in Chicago when the school year ends in June. She will send the difference between whatever he has saved up and the price of fare. A job as a hotel elevator boy is waiting for him when he gets to Chicago. She needs Sandy to help her out financially since she is not making enough to live on as a trainee under a black hairdresser.

A week later Annjee sends a letter to Sandy with his fare because he can start working at his new job that Saturday. Sandy is on the train that night after having made arrangements to receive credit for the remainder of his school year and saying goodbye to a tearful Tempy, who worries that Chicago may lead to Sandy's moral downfall. He also has the chance to visit Mrs. Johnson a few weeks before to get all the news on all his old friends and reminisce about his time growing up in Hager's house.

When Sandy arrives in Chicago, his mother initially fails to recognize him.