Cahill Expressway is a 1962 painting by the Australian artist Jeffrey Smart. The painting depicts the Cahill Expressway, a motorway in inner Sydney. It is "considered by many to be one of his finest works" and "perhaps his best-known picture". The work has been described as "startling ... for its recognisability as an Sydney scene and doubly so for its timeless quality." The painting was acquired by the National Gallery of Victoria in 1963 and is part of its Australian art collection.