The push and pull factors of migration from rural western Kenya to two urban destinations is investigated in this research. The focus is on linking migration to poverty at the origin and whether the migration process reduces or increases poverty at the destinations. The study primarily adopted qualitative methods that were geared towards revealing the phenomenological experiences of migration from Siaya and Vihiga counties in western Kenya to the cities of Kisumu and Nairobi, in relation to poverty. Out-migration in Western Kenya, mainly from the Siaya and Vihiga counties, is directed towards the regional city of Kisumu and the national capital of Nairobi city, which for long has been the country’s primate city. Under development in western Kenya and the desired lifestyle of the cities drive both rural-urban migration and rural-rural migration to the county’s economic hubs that rely on commercial agriculture. Siaya and Vihiga are two contrasting counties. Siaya has vast landscapes wallowing in poverty due to subsistence agriculture whereas Vihiga is unsuitable for agriculture because of large boulders occupying much of the cultivable land.