Ionic liquid (IL) interfaces with vacuum and water are studied by means of classical molecular dynamics simulations. Five ILs are compared: [C(2)mim][TfO], [C(12)mim][TfO], [C(2)mim][NTf2], [C(8)mim][NTf2] and [C(12)mim][NTf2], where [C(2)mim], [C(8)mim] and [C(12)mim] stand for 1-ethyl-, 1-octyl- and 1-dodecyl-3-methylimidazolium cation. Physical properties-density, thermal expansion coefficient, compressibility, surface tension, heat of vaporization, self-diffusion coefficient, electric conductivity and viscosity-are calculated and validated against experimental values. The structure of the interfaces is compared in terms of the orientation of the molecules and segregation into layers. It is observed that ILs with short alkyl chains orient at the surface; however, there is no single preferred orientation. ILs with longer chains, on the other hand, orient with alkyl chains protruding into the vacuum at the IL/vacuum interface and into the bulk IL, at the IL/water interface. Anions and water molecules tend to associate with polar imidazolium groups.