Nonlinear dynamic characteristics of a rotor-bearing system with cubic nonlinearity are investigated. The comprehensive effects of the unbalanced excitation, the internal clearance, the nonlinear Hertzian contact force, the varying compliance vibration, and the nonlinear stiffness of support material are considered. The expression with the linear and the cubic nonlinear terms is adopted to characterize the synthetical nonlinearity of the rotor-bearing system. The effects of nonlinear stiffness, rotating speed, and mass eccentricity on the dynamic behaviors of the system are studied using the rotor trajectory diagrams, bifurcation diagrams, and Poincaré map. The complicated dynamic behaviors and types of routes to chaos are found, including the periodic doubling bifurcation, sudden transition, and quasiperiodic from periodic motion to chaos. The research results show that the system has complex nonlinear dynamic behaviors such as multiple period, paroxysmal bifurcation, inverse bifurcation, jumping phenomena, and chaos; the nonlinear characteristics of the system are significantly enhanced with the increase of the nonlinear stiffness, and the material with lower nonlinear stiffness is more conducive to the stable operation of the system. The research will contribute to a comprehensive understanding of the nonlinear dynamics of the rotor-bearing system.