Transforming Education Through the Arts and Media (TEAM) is an arts integration program based on the concept of the 21st century transliterate learner who acquires knowledge and interacts across a range of tools, platforms, and media. Over a period of four years, TEAM was implemented in seventh- and eighth-grade classrooms by the Center for Community Arts Partnerships (CCAP) at Columbia College Chicago in collaboration with Chicago Public Schools (CPS). The purpose of this report is to present TEAM's successes and challenges and to share insights regarding strategies to ensure that teachers will continue to utilize media arts integration on their own when they are no longer collaborating with teaching artist partners. Pre- and post-residency surveys were administered each year to teachers to gather information on how they used media arts and technology in their classrooms, their capacity to integrate media arts and technology, their perceptions of their students' growth in media arts skills, and their perceptions of the teacher-teaching artist collaboration. Pre- and post-residency surveys were also administered to students.