This paper aims to investigate 21st Century Learning conducted at the University of Chicago Laboratory Schools in order to contemplate the future of art education in Japanese school education based on the direction given by the Ministry of Education, Culture, Sports, Science and Technology for the next revision of the course of study guidelines. This study analyzed a case introduced in Gina Alicia’s lecture “Experiential Learning Through Art” based on its relationship to Dewey’s educational philosophy, speech given at the lecture conference themed “American Educational Reform and Redesign of School Education—21st Century Learning at the University of Chicago Laboratory Schools” hosted by the Research Initiative for Developing Learning Systems (RIDLS) at Hiroshima University on July 2 and 5, 2016. Art education at the University of Chicago Laboratory Schools can be characterized by (1) promotion of learning to cultivate aesthetic literacy linked to experience, (2) promotion of learning to cultivate ideas and emotions through creative thinking with reflection, and (3) promotion of learning to achieve an organic connection with society. In conclusion, this study has examined the contemporary significance of art education at the University of Chicago Laboratory Schools in relationship with the three qualities and abilities “individual knowledge/skills,” “thinking skills, judgment skills, and expression skills,” and “ability to face humanity and learning,” which are the pillars for structural review of educational curriculum indicated in the “discussion points organization” of the Curriculum Planning Special Committee.