As a leading travel marketplace, Skyscanner is serving a daily load of up to a dozen billion flight itineraries to its users across the globe. The distribution of travel quotes at such a scale requires caching mechanisms optimized for minimizing the load on the partners (airlines and travel agencies) and maximizing the relevance and comprehensiveness of the itineraries to the travelers. This talk is focused on using data mining approaches for optimizing dynamic content distribution at scale and Skyscanner's efforts in this direction.