In the spring of 2014, Chicago educators met to reflect on the opportunities and challenges for progressive, democratic education in Chicago-area schools. This article weaves together the writings of teachers and principals from over 15 public schools and a couple of private and parochial schools who are thinking about their own experiences in relation to what they learn of Mission Hill, a public progressive school in Boston. Through these diverse voices--Chicago counterparts of the diverse voices of Boston's Mission Hill School--discussing testing, teacher evaluation methods, classroom practice, and school culture, possibilities emerge for educators seeking to expand and deepen progressive practice in urban schools. Relationships of trust and respect, courageous action, and finding the cracks all prove important in the process.