Hewa Chikakiyo served as a bushō from the latter part of the Sengoku period to the early Edo period. He was a retainer of the Chōsokabe clan and was based in Hewa Castle in Tosa Province.
Chikakiyo was born as the eldest son of Hewa Chikatake, a retainer of the Chōsokabe clan.
His father, Chikatake, was the son of Chōsokabe Kuniyasu (the younger brother of Chōsokabe Kunichika). In 1569, after being appointed by his lord, Chōsokabe Motochika, to serve as the lord of Hewa Castle, Chikatake adopted the surname of Hewa, which was passed on to Chikakiyo.
In 1600, at the Battle of Sekigahara, the Chōsokabe clan supported the Western Army, which lost to the Eastern Army led by Tokugawa Ieyasu. Consequently, the Chōsokabe were removed by the Tokugawa from their position as the sengoku daimyō of Tosa. Chikakiyo argued in favor of holing-up and mounting a resistance to the Tokugawa, but his proposal did not gain support. Later, at the Siege of Ōsaka, Chikakiyo hastened to join his former lord, Chōsokabe Morichika on the side of the Toyotomi forces. At the Battle of Yao, he made contributions serving in the second division of spear-wielding soldiers.
After the fall of Ōsaka Castle, Chikakiyo strayed from Morichika at Yawata in Yamashiro Province and then served Tōdō Takatora, receiving a fief of 150 koku. During the Siege of Ōsaka, the Chōsokabe and Tōdō forces engaged in frontal assaults against one another. Numerous retainers fighting for the Tōdō army formerly served the Chōsokabe clan, so, in addition to knowing of Chikakiyo from the battles, he had many acquaintances among the Tōdō forces.
Chikakiyo learned a sword-fighting style known as shinkageryū that was taught by Kamiizumi Nobutsuna. Skilled in the art, Chikakiyo then created the Hewa style. In 1634, when Araki Mataemon went to Ueno in Iga Province to commit a revenge killing, his own sword broke when struck during the clash by a wooden sword. When he later visited the Tōdō, Chikakiyo criticized him for carrying a sword that could easily break on such an important mission. Embarrassed at his lack of insight, in 1635, Mataemon became a disciple of Chikayoki and learned the shinkageryū style from Chikakiyo. Members of the Hewa family served as sword instructors for the Tōdō domain and taught the shinkageryū (Hewa) style of swordsmanship.