After appearing in a musical revue in Chicago, she won a vocal competition in 1927 which provided her with a scholarship to train as an opera singer at the Bel Canto Studio, Inc. of New York.
She notably translated Eugene Zador's opera Christopher Columbus from German into English for the work's world premiere in 1939.
[15] Chekova had a minor part in the ensemble of the 1931 Broadway revival of John N. Raphael and Constance Collier's Peter Ibbetson at the Shubert Theatre.
[19] In 1934 Chekova was engaged at Radio City Music Hall (RCMH) where she sang works by Rudolf Friml is a stage show that also featured The Rockettes.
[20] She also performed the title role in Giacomo Puccini's Madama Butterfly at the RCMH in May 1934 with Edwina Eustis as Suzuki and Alfredo Gandolfi as Sharpless.
[24] Chekova was engaged with the touring San Carlo Opera Company for the 1935–1936 season in which she performed the role of Nedda in Pagliacci, Marguerite in Faust and Micaëla in Carmen.
[28][29] In 1939 Chekova portrayed Leonora in Il trovatore opposite Florence Foster Jenkins as Azucena with the Verdi Club in New York City,[30] and returned to the RCMH as Musetta.
[31] Chekova translated the original German language libretto to Eugene Zador's opera Christopher Columbus (1939) into English, and it is her translation of the libretto that was used when the work was given its world premiere on October 8, 1939 in a concert version of the work at the Center Theatre with Robert Weede in the title role.
It was performed not only for a live radio broadcast on the NBC Blue Network program Music Hall of the Air but also in front of a sold out audience at the theatre.