This article investigates the role of the notion of freedom in Hegel’s Philosophy of Art by isolating the particular way Hegel frames this concept within the aesthetic context. While Hegel’s notion of freedom is certainly rooted in logic and acquires some of its basic features thanks to the anthropological and moralpolitical inquiry, it is not reducible to these fields. Indeed, by analyzing the most relevant moments of freedom in the Hegelian Lectures on Aesthetics and underscoring the variations in the definition of freedom both in Hegel’s treatment of the different forms of art (symbolic, classic, romantic) and in the individual arts (from architecture to poetry), I argue that Hegel makes a crucial distinction between two important meanings of freedom, which I will isolate. The first one is appropriate to the notion of art, particularly the art typical of the classical age (and of the sculpture), the second one is a higher version of freedom – one that is more spiritual, less artistic, but still included in the aesthetic domain – which is typical of the modern era (and of the poetry). The crucial difference between these two meanings of freedom is determined by the appearance of the free subjectivity. I conclude the article by illustrating how the notion of freedom becomes decisive, especially in modernity, in determining the highest aim of art.