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When magic enables Zack's eighty-eight-year-old grandmother to become a terrific batter, she ends up playing in a Chicago White Sox baseball game.

Willie, a boy growing up on the north side of Chicago in 1942, is disheartened when a neighbor tells him his skin color prohibits him from ever realizing his dream of playing professional baseball, but his hopes are revived when he sees an exhibition game at Wrigley Field between an astonishing Negro League team and players from the Major Leagues.

High school freshman Ryan Walsh, a Chicago Cubs fan, meets Nick when they both skip school on opening day, and their blossoming relationship becomes difficult for Ryan when she discovers that Nick is seriously ill and she again feels the pain of losing her father five years earlier.

Unable to make friends at her new school, Rosie learns that one of Chicago's baseball teams has lost its top player and disguises herself as a boy to take his place.

At the turn of the twentieth century, the Travelin' Nine baseball team travels to Chicago to play another game to earn money to pay off the Payne family's debts, and have another confrontation with the Chancellor.

During a visit to the Chicago Cubs' Wrigley field, cousins Mike and Kate investigate why someone has been tampering with the famous ivy vines growing on the outfield walls.

The trip to Chicago for Griffith, Ruby, and Graham becomes an adventure in itself after they realize their Uncle Owen has gone missing and the Chancellor has set his sights on the money the Travelin' Nine have been trying to raise.