In this article, a methodology of chattering analysis of Sliding Mode/Higher Order Sliding Mode (SM/HOSM) control systems in the frequency domain is presented. A numerical method for computing the Describing Functions (DFs) of HOSM control algorithms is given. The algorithm for predicted chattering parameters in dynamically perturbed system via the Describing Function-Harmonic Balance (DF-HB) technique is proposed. The stability conditions for limit cycles in dynamically perturbed HOSM control systems are presented. The concepts of Practical Stability Phase Margin (PSPM) and Practical Stability Gain Margin (PSGM) as the robustness metrics to unmodeled dynamics in HOSM control systems are introduced. The methodologies for computing PSPM and PSGM via DF-HB technique are provided. The accuracy of the proposed chattering analysis techniques is confirmed via computer simulations.