A hydraulic cylinder includes a piston that defines a driving pressure chamber and a cushion pressure chamber within a cylinder tube, an air chamber defined inside a hollow piston rod, an orifice that leads a working fluid in the cushion pressure chamber into the air chamber when the cushion pressure chamber contracts during an extension operation, a check valve that returns a working fluid in the air chamber to the driving pressure chamber when a differential pressure between the air chamber and the driving pressure chamber rises to or above a predetermined value, and a valve housing that houses the check valve. A throttle gap is defined between an outer peripheral surface of the valve housing and an inner peripheral surface of the piston rod, and a working fluid ejected from the orifice during the extension operation flows into the air chamber through the throttle gap.