Born Chigusa Kitani at Kita-ku, Osaka Dōjima (ja:堂島), the center of the Osaka (the second largest metropolitan area in Japan), in 1895 under the name Ei Yoshioka (吉岡 英, Yoshioka Ei).

While studying at Shimizudani Girls' High School, She studied Bird-and-flower painting under Chokujō Fukada (ja:深田直城, Fukada Chokujō) who is a famous painter of the Shijō school (四条派, Shijō-ha).

She trained in Seattle, Washington, in the United States for two years from the age of 13, and her work was exhibited throughout Japan.

In the same year, she established a painting school Yachigusa-kai (八千草会) and Chigusa-kai (千種会) at her home in Osaka.

In 1915, Chigusa Kitani, at the age of 20, was selected for the first Osaka Fine Arts Exhibition (大阪美術展覧会, Osaka Bijutu Tenrankai) as Shin-kyo (新居, "New house") and for the 9th Ministry of Education Art Fine Arts Exhibition (文部省美術展覧会 (文展, Bunten), Monbu-Sho Bijutu Tenrankai)[5] as Hari-Kuyō (針供養, "Memorial ceremony Festival of Broken Needles").This Hari-Kuyō is a work depicting a Geisha girl in Kyoto.