Following the Flight of the Earls in 1607, Chichester was a leading figure during the Plantation of Ulster. Initially he intended that the number of Scottish planters would be small, with native Irish landowners gaining more land. However, after O'Doherty's Rebellion in Donegal in 1608, his plans changed and all the native lords lost their land. Most of the land was awarded to wealthy landowners from England and Scotland. However Chichester successfully campaigned to award veterans of the Nine Years' War land as well, funded by the City of London Livery Companies.