The urbanization of migrant workers is key to China’s social transformation from traditional agricultural society to modern urban society. To explore how personality, economic and professional mobility features, housing and social security, urban features and other elements influence new generation of migrant workers’ willingness to settle in the third- and fourth-tier cities of China, this paper makes cross-tabulation comparison and applies logistic regression model based on the micro-level data from the 2014 Dynamic Monitoring of the Floating Population in Yangtze River Delta, which is compiled by the NHFPC (National Health and Family Planning Committee) of the PRC. The result shows that: married migrants, aged 28 to 35 years old, with decent wages and business foundation, already owning homes and supported by social security to some extent, are more willing to settle in the local cities; industrial structure in the third- and fourth-tier cities of Yangtze River Delta is not attractive enough to trans-provincial migrants; domestic urban division system has made the new generation of migrant workers reluctant to settle in small cities. These findings will provide a new perspective to understand how government shall guide the new generation of migrant workers to settle in the third- and fourth-tier cities and help them realize their “urban dreams”.