The total cost of road construction comprises direct costs paid by agencies and indirect costs paid by road users. In densely populated urban areas, work zone instigated user costs could outweigh direct costs and therefore need to be considered in project alternative selection. This paper develops and applies a probabilistic methodology for quantifying user delay cost (UDC) for urban arterial work zones. The methodology incorporates traffic microsimulation and Monte Carlo simulation to establish a distribution of UDCs, which supports risk-based optimization of work zone configuration, justification of accelerated construction methods, and establishment of contractual incentives and disincentives. The paper demonstrates the development of the methodology through a bridge rehabilitation case study in Calgary, Alberta, Canada. The results revealed that every hour of work zone operation during the morning peak resulted in 169.2 h of network-wide vehicle delay and a mean UDC of CAD 2,816 (in 2016 Canadian dollars). To further demonstrate the applicability of the methodology, a second case study examined three work zone configurations and concluded that the traditional work zone configuration instigated the lowest UDC.