Migratory birds use numerous strategies to successfully complete twice-annual movements between breeding and wintering sites. Context for conservation and management can be provided by characterizing these strategies. Variations in strategy among and within individuals support population persistence in response to changes in land use and climate. We used location data from 58 marked Whooping Cranes (Grus americana) from 2010–2016 to characterize migration strategies in the U.S. Great Plains and Canadian Prairies and southern boreal region, and to explore sources of heterogeneity in their migration strategy, including space use, timing, and performance. Whooping Cranes completed approximately 3,900-km migrations that averaged 29 days during spring and 45 days during autumn, while making 11–12 nighttime stops. At the scale of our analysis, individual Whooping Cranes showed little consistency in stopover sites used among migration seasons (i.e., low site fidelity). In contrast, individuals expressed a measure of consistency in timing, especially migration initiation date. Whooping Cranes migrated at different times based on age and reproductive status, where adults with young initiated autumn migration after other birds, and adults with and without young initiated spring migration before subadult birds. Time spent at stopover sites was associated with migration bout length and time spent at previous stopover sites, suggesting Whooping Cranes acquired energy resources at some stopover sites that they used to fuel migration. Whooping Cranes were faithful to a defined migration corridor but showed less fidelity in their selection of nighttime stopover sites; hence, spatial targeting of conservation actions may be better informed by associations with landscape and habitat features rather than documented past use at specific locations. The preservation of variation in migration strategies existing within this species that experienced a severe population bottleneck suggests that Whooping Cranes have maintained a capacity to adjust strategies when confronted with future changes in land use and climate.