The city of Chkalovsk was founded in the 12th century under the name Vasilyeva Sloboda in honor of its founder, Prince Vasily Yuryevich, son of Yuri Dolgoruky. The settlement initially served as a backup defensive point for Gorodets. After Yuri Dolgoruky reclaimed the city of Little Kitez from the Cheremis, he renamed it Gorodets Radilov and appointed his son Vasily Yuryevich as the voivode. The city became a center of attraction for the local Mari population, and over time, the Mari people and their Russified descendants made up the majority of the residents. To protect against raids by Ugric peoples, Vasily built a fortress on the right bank, named Vasilyeva Sloboda.

In the 14th and 17th centuries, Vasilyeva Sloboda belonged to the Shuysky princes and was their ancestral estate. The last owner from the Shuysky family was Tsar Vasily IV Ivanovich. From 1610 to 1764, Vasilyeva Sloboda was owned by the Moscow Ascension Monastery and later became a state economic village.

In the 1950s, due to the construction of the Gorky Hydroelectric Power Station, a significant part of Chkalovsk found itself in a flood zone. Most houses had to be relocated, and a shipbuilding plant was constructed in the new location.

The Ascension Church, made of stone, was built in 1755. The main altar is dedicated to the Ascension of the Lord, the right chapel to the Annunciation of the Most Holy Theotokos, and the left to St. Nicholas the Wonderworker. The second church, also made of stone, was built in 1797 and is dedicated to St. Anastasia the Great Martyr.