An investigation is made of the classical nonlinear resonance and the classical stochastic dynamics of rays in waveguide media with irregular inhomogeneities. Analytic and numerical methods are used to study the characteristics of the ray trajectories, their confinement in a nonlinear resonance, and the development of chaotic behavior in waveguides with longitudinal periodic inhomogeneities. It is established that the localization of the rays has fractal properties; in particular, the cycle length of a ray and the time and velocity of propagation of a signal depend on the initial parameters of the ray in the form of a "devil's staircase." A waveguide with an inhomogeneous index of refraction and a periodically corrugated wall is considered.