Intermodal Trucking Chicago Jack Freeman Trucking Intermodal Trucking Chicago has been delivering general commodities in the Chicagoland area for more than 40 years. As one of Chicago's original drayage companies, Jack Freeman Trucking has the experience to handle your intermodal needs. With a selection of 20', 40', Triaxle, and eight pin chassis there is no container that we cannot handle. Intermodal Trucking Chicago Jack Freeman Trucking.