The driving environment of expressway maintenance work zones is complex and the rate of accidents is high. It is very important to improve road traffic safety, evaluate driving risks, and establish risk assessment models in maintenance work zones. In this paper, driving simulation experiments are used to analyze four factors of driving risk in the working area: vehicle flow density, control measures in maintenance work zones, alignment of road segment, and position of closed lane. Then the maintenance work zones are divided into three areas: warning area, interleaving area (confluence area and shunt area), and working area. A multiple regression model of driving risk in different areas is constructed. Finally, research objects are selected to verify the risk evaluation model with real vehicles, and the deviation between risk prediction value and risk actual value is about 7% and 9%, which proves that the risk evaluation model is effective.