A cup holder is mountable onto the top of an extendable handle projecting from the top of a piece of wheeled luggage. The cup holder holds a cup of liquid while the luggage is being pulled around. The cup holder is constructed from a stretchy fabric with a handle sleeve that resiliently grips the top of the extended luggage handle. The flexibility of the fabric material provides the cup support, in the form of a truncated hollow cone, with a way of rotating freely with respect to the luggage handle so that a self-leveling action is provided without need of a mechanical hinge.