Baseball and Hollywood have a long history both on screen and in real life where movie stars can be seen dating ballplayers. J.Lo and ARod being a recent example, though the most famous couple was probably Marilyn Monroe and Joe DiMaggio. As far as stadiums go, the home of the Chicago Cubs has appeared in more movies than most. Below you can find a list that includes many of the movies filmed at Wrigley Field.
Rookie of the Year is definitely the movie with the most Cubs baseball in it. The plot centers around a kid who pitches for the Cubs.