Chkalov studied in the technical school in Cherepovets but later returned to his home town to work as an apprentice in the shipyard alongside his father.

In 1936 and 1937, he participated in several ultra long flights, including a 63-hour flight [ru] from Moscow, Soviet Union to Vancouver, Washington, United States via the North Pole in a Tupolev ANT-25 airplane (18–20 June 1937), a non-stop distance of 8,811 kilometres (5,475 mi).

Chkalov died on 15 December 1938 while piloting a prototype of the Polikarpov I-180 fighter, which crashed during its maiden test flight.

Neither of the aircraft's two chief designers, Nikolai Polikarpov and Dmitry Tomashevich, approved the flight, and no one had signed a form releasing the prototype from the factory.

The official government investigation concluded that the engine cut out because it became too cold in the absence of the cowl flaps.

Years later, fellow test pilot Mikhail Gromov blamed the designers for flawed engine cooling and Chkalov himself for deviating from the flight plan.

Chkalov's son claimed that a plan to assassinate his father had been in the works in the months preceding his death, but the circumstances of the crash make foul play unlikely.

The metro rail systems of Moscow, Saint Petersburg, and Nizhny Novgorod each have a Chkalovskaya station.

A musical duet, Отряд имени Валерия Чкалова ("Detachment named after Valery Chkalov"), recorded their first album in 1983.

One of them located in the city of Chișinău, is most well known for its comically short length of 41 meters making it the shortest street in the country.