A system and a method for automatically packaging item(s) are disclosed, as well as associated packages. The method includes generally four steps. First, an outer tray containing one or more item(s) is received. Second, an inner tray is placed in the outer tray over the one or more item(s), and the inner tray includes a plurality of preformed columnar compartments. Third, the inner tray and the outer tray are sealed to form at least a partial vacuum between an exterior surface of the inner tray and an interior surface of the outer tray. The item(s) are firmly secured in the at least partial vacuum such that the item(s) will not shift within the package during shipment. Fourth, a cover is placed over the inner tray to close the plurality of preformed columnar compartments to thereby form a plurality of air compartments, which collectively protect the item(s) from external impact.