Providing insurance contract with “deductible” is beneficial for both insurer and insured. In this paper, we provide a utility modeling approach to handle insurance pricing and evaluate the tradeoff between discount benefit and deductible level. We analyze four different pricing problems of no insurance, full insurance coverage, insurance with β% deductible and insurance with D-dollar deductible based on a given utility function. A numerical example is also used to illustrate some interesting results.