Chip Nottingham received his undergraduate degree from Wesleyan University, with a major in history, and then worked for three years in the field of environmental policy and regulatory issues at the U.S. Department of Justice, at a private law firm, and as a legislative consultant for the American International Group, an international insurance company. After earning his law degree from George Mason University School of Law in Arlington, Virginia, he served as youth campaign advisor, counsel and chief of staff for Republican Congressman Tom Davis of Virginia; chief of staff for Republican Congressman Bob Goodlatte of Virginia; assistant secretary of transportation, and commonwealth transportation commissioner for Virginia Governor Jim Gilmore, also a Republican; as chief executive officer of the Virginia Department of Transportation; as counsel to the U.S. House of Representatives Committee on Government Reform; and as associate administrator for policy and governmental affairs at the Federal Highway Administration. Nottingham was sworn in as Chairman of STB on August 14, 2006. He served until March 2009 when he moved down to Vice Chairman to make way for President Barack Obama's choice of Chairman.

Nottingham has been a consistent contributor to the Republican National Committee, and to Republican campaigns, particularly Friends of George Allen and Tom Davis for Congress, both in Virginia, where Nottingham resides. In addition, in 2004 Nottingham gave to the Bush-Cheney Compliance Committee and the Bush-Cheney Primary, and in January 2008 he contributed to John McCain.