There is a growing interest in the use of ionic liquids to provide lubrication for challenging contacts. This study is an initial assessment of the application of two ionic liquids based on choline chloride cations to be used as ionic liquid lubricants for engineering contacts, in this case steel on steel. These ionic liquids, termed ethaline and reline, have anions of ethylene glycol and urea, respectively, and are available at relatively low costs and in high quantities. In order to assess the lubrication performance of the ionic liquids, lubricated reciprocating sliding wear tests were conducted between M2 tool steel samples and a steel stylus. Initial tests conducted at a sliding speed of 0.005 m s−1 and 30 N showed that ionic liquids could provide low friction lubrication, comparable to that of SAE 5W30 friction modifier free engine oil under the same test conditions; however, lubrication was lost after short sliding distances. Further testing with higher sliding speed/lower load and varying sample surface textures showed that ionic liquid lubrication could be better maintained in high-speed/low-load testing and by increasing the roughness and therefore surface area of the sample. It was also observed that the choline chloride/urea ionic liquid formed a residual film when tested on iron silicate peened samples, and that this film may promote lubrication.