He represented Kenya at the 2004 Athens Olympics and reached the final but failed to finish the race. Chebii won the individual and team silver medals in the short race at the 2005 IAAF World Cross Country Championships. He has won a number of races on the athletics circuit including the Cross Internacional de Itálica in 2002 and the Great Ireland Run in 2007 and 2008. He gained selection for the 5000 m at the 2009 IAAF World Athletics Final and came in ninth place.