It depends on two key factors – your deductible amount and the cost of a new windshield. As a general rule, if your deductible is less than the out-of-pocket cost of a windshield replacement, it is economically more sensible to go through insurance. For example, if your deductible is $250 and the windshield replacement cost is $550, using insurance means you pay only the deductible, saving $300. Conversely, if your deductible exceeds the windshield’s cost, paying out of pocket is a better option.