Systems, methods and media are provided for optimizing similar item recommendations in a semi-structured environment. In one embodiment a system includes at least one processor and a memory storing instructions that, when executed by the at least one processor, cause the system to perform operations comprising, at least identifying a seed item; retrieving a subset of recommended items relevant to the seed item; and ranking the subset of recommended items based on an item conversion probability, wherein the ranking of the subset of recommended items is based on a machine learning technique, and wherein a binary or multi-class label is used as training input to the machine learning technique.