Chris Van Allsburg won the Randolph Caldecott Medal for Caldecott Medal twice (1982, 1986).
| Year | Contest | Category | For | Sources |
|---|---|---|---|---|
| 1986 | Randolph Caldecott Medal | Caldecott Medal | The Polar Express | 1 · 2 |
| 1982 | Randolph Caldecott Medal | Caldecott Medal | Jumanji | 1 · 2 |