Chaskin has worked with the Chapin Hall Center for Children at the University of Chicago since 1990. He is currently a Research Fellow there and serves as the Director of the center's International Program.
Chaskin has received a variety of research grants; funders have included the City of Chicago, the Ford Foundation, the John D. & Catherine T. MacArthur Foundation, the Chicago Community Trust, the W.T. Grant Foundation, the Annie E. Casey Foundation, and the Save the Children Foundation. He also is widely published in journals and books on the subjects of community building and community capacity.