This study investigates a deep connection between Japanese characters and Ikebana, which is due to the fact that Japanese characters as well as ikebana express the same picture of the world. Because the basis of this model of the world is laying in the Chinese tradition, we will first examine the Chinese characters and Chinese art of flower arrangement or chahua, and then the Japanese characters and Japanese ikebana. In the study, we refer not only to the works of Russian researchers, such as V.V. Malyavin, V.G. Belozyorova and V.A. Pronnikov, but, to a greater extent, to sources in Japanese (Nakamura Yasuo, Sasaoki Ryuho, Kumakura Isao, etc.), as well as to English-speaking authors or translations (Li Xia, Li Huilin). Analyzing the structure of the Chinese character, we look at lined paper for calligraphy which is usually being used in China. Lines of this paper indicate the connection of the structure of a character with Taiji or Supreme Ultimate, because a character is inscribed in a circle of Taiji, it has Yin and Yang sides and as we can say ‘exists’ in the ‘circle of changes’ or Bagua. In Japan, Chinese lined paper were not widespread, but the styles of calligraphy (regular script, semi-cursive script, cursive script) that came from China were elevated to the principle of simplified and broken form, Shin – Gyo – So, which became the basis for the Japanese type of beauty, kuzushi-no bi. Then we turn to the Chinese flower art, chahua and show its basic principle, which related to the Chinese characters, we mean the balance of Yin and Yang. Japanese art of ikebana we analyze in more detail and observe three main schools of Ikebana: Ikenobo, Ohara and Sogetsu. In the schemes of the Ikenobo (the oldest school in Japan), we find schemes in which floral arrangements are inscribed in a circle of Taiji (rikka flowers). In a later direction of Japanese flower arrangement (shoka, or seika flowers), we meet the principle of Shin – Gyo – So. We consider the same principle on the example of chabana, that is, flower arrangements for a tea ceremony. We also observe ikebana of Japanese literati Bunjin, who strive for a lifestyle of Chinese literati Wenren. The flowers in Chinese taste in contrast with actually Japanese ikebana do not have any patterns, but it has ‘refined riddle theme’ meigogadai with limited combinations of flowers. Also, it has more obvious connection with Chinese characters form. We conclude that a Chinese character shows subtle difference between manifested and unmanifested world, balance of Yin Yang while in Japanese tradition we can see preference of forms broken or simplified with Shin Gyo So. Chinese flower arrangement сhahua is also based on Yin Yang balance while in Japanese Ikebana it was transformed with Shin Gyo So.