One of the main themes of the play is the effect social change has on people. The emancipation of the serfs on 19 February 1861 by Alexander II allowed former serfs to gain wealth and status while some aristocrats were becoming impoverished, unable to tend their estates without the cheap labor of slavery. The effect of these reforms was still being felt when Chekhov was writing forty years after the mass emancipation.
Chekhov originally intended the play as a comedy (indeed, the title page of the work refers to it as such), and in letters noted that it is, in places, almost farcical. When he saw the original Moscow Art Theatre production directed by Konstantin Stanislavski, he was horrified to find that the director had moulded the play into a tragedy. Ever since that time, productions have had to struggle with this dual nature of the play (and of Chekhov's works in general).
Ranevskaya's failure to address problems facing her estate and family mean that she eventually loses almost everything and her fate can be seen as a criticism of those people who are unwilling to adapt to the new Russia. Her petulant refusal to accept the truth of her past, in both life and love, is her downfall throughout the play. She ultimately runs between her life in Paris and in Russia (she arrives from Paris at the start of the play and returns there afterwards). She is a woman who lives in an illusion of the past (often reliving memories about her son's death, etc.). The speeches by the student Trofimov, attacking intellectuals were later seen as early manifestations of Bolshevik ideas and his lines were often censored by the Tsarist officials. Cherry trees themselves are often seen as symbols of sadness or regret at the passing away of a certain situation or of the times in general.
The idea of independence and freedom is highly prevalent when the reader takes a look at Firs and Lopakhin. Firs has been with the estate for decades, and all he's ever known is to serve his masters. When the news of the Orchard being closed, Firs seems unfazed by the news, and continues to maintain his duties, he is unable to find his independence and freedom, however; Lophakin was able to "free" himself. In the sense that he was able to find motivation to keep on going. Even though the two are polar opposites on the social ladder, they both have internal struggles regarding what their life is going to be after the Orchard closes.
The theme of identity, and the subversion of expectations of such, is one that can be seen in The Cherry Orchard; indeed, the cast itself can be divided up into three distinct parts: the Gayev family (Ranevskaya, Gayev, Anya and Varya), family friends (Lopakhin, Pishchik and Trofimov), and the "servant class" (Firs, Yasha, Dunyasha, Charlotta and Yepikhodov), the irony being that some of them clearly act out of place – think of Varya, the adopted daughter of an aristocrat, effectively being a housekeeper; Trofimov, the thinking student, being thrown out of university; Yasha considering himself part of the Parisian cultural élite; and both the Ranevskayas and Pishchik running low on money while Lopakhin, born a peasant, is practically a millionaire.
In a Marxist view of the play, Lopakhin represents the emergent post-emancipation bourgeois landholder and businessman reaping revenge on his old masters, Ranyevskaya and Gayev represent the infantile social character of a declining feudal order, and the chopping down of the cherry orchard to erect summer villas represents the violent changes of modernization. An alternative view is that The Cherry Orchard was Chekhov's tribute to his own oeuvre. Many of the characters in the play harken back to his earlier works and are based on people he knew in his own life. It should also be noted that his boyhood house was bought and torn down by a wealthy man whom his mother had considered a friend. Finally, the classic "loaded gun" that appears in many of Chekhov's plays appears here, but this is his only play in which a gun is shown but not fired.