The phenolic composition of wine depends on, among other factors, the grapes used to make it. In this sense, knowledge of the chemical composition of grapes and its association with the resulting wines is an important tool to determine if there is a relationship between the phenolic composition of grapes and the price that these wines obtain in the market. For this purpose, grape skins and seeds from the cultivar Cabernet Sauvignon from the central region of Chile, in 2009 and 2010 vintages from two ripening points, were subjected to chemical and phenolic analyses, as were the wines made from these grapes. Grapes and the corresponding wines from three retail price wine categories, U.S. $6-8, U.S. $28-30, and U.S. $150-160, were evaluated. No differences were found across the price categories in the chemical analysis of grapes. Berry skins and wines from the higher price categories presented a higher concentration only of total tannins, and the differences in their concentrations were only among the different fractions of proanthocyanidins in the skins, seeds, and wines; there were no differences in their proportions. A seasonal effect influenced the concentrations of certain compounds in grapes and led to a decrease in the concentration of total phenols, total tannins, and total anthocyanins between sampling dates as harvesting moved toward the common commercial grape harvest in Chilean viticulture.