This paper aimed to investigate how today’s University of Chicago Laboratory Schools succeeds with John Dewey’s educational philosophy and promotes educational practices, based on a presentation by Principal Sylvia Anglin at the lecture conference “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. For the characteristics of operation policy of the Lower School at the University of Chicago Laboratory Schools, in addition to investigating with a focus on (1) educational philosophy, (2) curriculum, and (3) teacher expertise, I also clarified the relationship with Dewey’s educational philosophy through analysis of the “Playground Construction Project,” which is a practical example of 21st Century Learning being developed at the Laboratory Schools. In conclusion, I discussed the contemporary significance of art education based on the direction of the next revision of the course of study guidelines.