The fundamental role of cholesterol in the regulation of eukaryotic membrane structure is well-established. However the manner in which atomic level interactions between cholesterol and lipids, with varying degrees of chain unsaturation and polar groups, affect the overall structure and organization of the bilayer is only beginning to be understood. In this paper we describe a series of Molecular Dynamics simulations designed to provide new insights into lipid-cholesterol interactions as a function of chain unsaturation. We have run simulations of varying concentrations of cholesterol in dipalmitoyl phosphatidylcholine (DPPC), palmitoyl-oleyol phosphatidylcholine (POPC), and dioleyol phosphatidylcholine (DOPC) bilayers. Structural analysis of the simulations reveals both atomistic and systemic details of the interactions and are presented here. In particular, we find that the minimum partial molecular area of cholesterol occurs in POPC-Chol mixtures implying the most favorable packing. Physically, this appears to be related to the fact that the two faces of the cholesterol molecule are different from each other and that the steric cross section of cholesterol molecules drops sharply near the small chain tails.