The correlation between architectural designs and paintings created by the distinguished architect and painter Chen Chi-Kwan has not yet been well discovered. To make up for this gap, this article methodologically contextualizes Chen’s paintings and early architectural designs together within the trends of Analytical Cubism and Architectural Modernism developed in the first half of the 20th century. Three crucial writings in understanding this correlation are identified as Space, Time and Architecture: The Growth of A New Tradition, Language of Vision, and Transparency: Literal and Phenomenon. By analogously comparing Chen’s architectural designs and paintings, the author points out that, first of all, via overlapping figure and ground, Chen experimented on the visual perception of excision and extension. Second, Chen played with “phenomenal transparency” and created spatial ambiguity. Although under apparent Western influences, Chen tried his own brand new ways of expression. Third, the concept of “literal transparency” and multi-layered space could also be seen in Chen’s works. However, certain special techniques he adopted not only redefined the materiality of glass, but also challenged the conventional ways of Chinese painting and building. Inspired by but not limited to Western Modernism, Chen Chi-Kwan developed his own spatial and visual languages with cultural characteristics. As two kinds of medium in exploring the same new spatial concept of transparency, architectural designs and paintings are complementary and equally satisfactory in result to Chen Chi-Kwan.