Designing new ionic liquids (ILs) is of crucial importance for various industrial applications. However, this always leads to a daunting challenge, as the number of possible combinations of cation and anion are very high and it is impossible to experimentally propose and screen a wide pool of potential candidates. However, recent applications of machine learning (ML) models have greatly improved the overall chemical discovery pipeline. In this study, we compare different generative methods for producing ionic liquids. In this comparison, we show the following: (1) when training data is scarce, a transfer learning approach can be applied to variational autoencoders (VAEs) to generate molecular structures of the target molecule type; (2) in a VAE-like structure, separate latent spaces for the cationic and anionic moieties can result in meaningful representations for their combinative, macroscopic properties; (3) interpolating between ILs with desired properties can result in a new IL with attributes similar to the two structural end points.