Aircraft dynamics are dominated by nonlinearities that may drive the aircraft into chaotic motions under certain conditions. Past studies in this area have explored several factors leading to the evolution of chaotic dynamics. However, a proper route or sequence for the evolution of chaotic dynamics has not been adequately substantiated. In this context, this paper systematically examines possible routes to chaos in the post-stall dynamics of an F-18 High-Alpha Research Vehicle model with external steady wind as the driving agent. Using tools from nonlinear dynamics based on bifurcation analysis, phase portrait, Poincaré map and amplitude spectrum analysis techniques, existence of quasi-periodic, period-doubling and intermittency routes to chaos are established. An eighth-order nonlinear aircraft model incorporating wind effects has been used for generating time responses from different post-stall flight conditions. © 2020, Springer Nature B.V.