Cyclistic is a Chicago-based bike-share company offering flexible transportation options through single-ride passes, full-day passes, and annual memberships. While these pricing models have driven strong growth and attracted a diverse customer base, internal analysis shows that annual members generate greater long-term value than casual riders. This case study analyzes historical Cyclistic bike-share trip data to explore behavioral differences between casual riders and annual members. The findings provide actionable, data-driven insights to support marketing strategies aimed at increasing membership conversions and driving sustainable business growth.