Craik was elected as a Federalist to the Fourth Congress to fill the vacancy caused by the resignation of Jeremiah Crabb; he was reelected to the Fifth and Sixth Congresses and served from December 5, 1796, to March 3, 1801; again appointed chief justice of the fifth judicial district of Maryland and served from October 20, 1801, to January 28, 1802. He resided in Frederick, Maryland, and died prior to 1814.