The process of migration has been the subject of extensive debates throughout Europe. Migration patterns are constantly changing in our current globalized economy; therefore, it is insufficient to assume that countries sharing cultural, geographical, and linguistic similarities experience synchronised migration flows. This article attempts to contribute to the understanding of one of the most dominant migration streams from Eastern Europe, specifically the movement from Ukraine to the Czech Republic and Poland. The period of interest follows the accession of the destination countries into the EU between 2004 and 2014. The results show that Ukraine suffers from much worse economic and social conditions than Poland and the Czech Republic. GDP growth, unemployment, and the poverty rate are three important indicators that explain why there has been such a large influx of Ukrainians into the host countries. While educational attainment was also massively deficient in Ukraine, it appears this is a reflection of the institutional failure of the Ukrainian education system, thus leading to the education–occupation mismatch of Ukrainian migrant workers. Despite the fact that Poland and the Czech Republic are linguistically, culturally, and geographically close, the immigration flow from Ukraine has behaved very differently in each case; for instance, the most notable contrast reveals that migration to the Czech Republic, but not to Poland, was substantially affected by economic crises.