Ionic liquids (ILs)─salts in a liquid state─play a crucial role in various applications, such as green solvents for chemical synthesis and catalysis, lubricants, especially for micro- and nanoelectromechanical systems, and electrolytes in solar cells. These applications critically rely on unique or tunable bulk properties of ionic liquids, such as viscosity, density, and surface tension. Furthermore, their interactions with different solid surfaces of various roughness and structures may uphold other promising applications, such as combustion, cooling, and coating. However, only a few systematic studies of IL wetting and interactions with solid surfaces exist. Here, we experimentally and theoretically investigate the dynamic wetting and contact angles (CA) of water and three kinds of ionic liquid droplets on hydrophobic microstructures of surface roughness (r = 2.61) and packing fraction (ϕ = 0.47) formed by micropillars arranged in a periodic pattern. The results show that, except for water, higher-viscosity ionic liquids have greater advancing and receding contact angles with increasing contact line velocity. Water drops initially form a gas-trapping, CB wetting state, whereas all three ionic liquid drops are in a Wenzel wetting state, where liquids penetrate and completely wet the microstructures. We find that an existing model comparing the global surface energies between a CB and a Wenzel state agrees well with the observed wetting states. In addition, a molecular dynamic model well predicts the experimental data and is used to explain the observed dynamic wetting for the ILs and superhydrophobic substrate. Our results further show that energy dissipation occurs more significantly in the three-phase contact line region than in the liquid bulk.