From a young age, Cheqara was drawn to music and poetry, being influenced by his father, who gave him his first oud. Cheqara was also influenced by the Zawia Al-Harraqiya sufi movement, which practises devotion to Allah through the performance of Andalusian music. Many of the songs are also about beautiful Andalusia, beautiful women and good wine, remindful of the Al-Andalus period. By the age of fourteen, Cheqara already performed in a band, meeting Abdessalam Allouch, who taught him malhoun (the Arabic art of sung poetry).
Cheqara sang Andalusian and traditional Moroccan folksongs in mawawil (improvised solo), inshad (solo) styles, and his band was famous for their live instrumental improvisation (taqsim). Many of his songs were based on poetry and folklore passed through families in Tetuan.
In the 1940s, Cheqara travelled extensively in Morocco, performing with noted Moroccan musicians.In 1940, along with other artosts, he petitioned the Kalifa Mulay Hassan Ben Mahdi for a conservatorium for Morocco’s Andalusian musical heritage. The conservatorium was founded as the Hasani Conservatory of the Moroccan Music. After several name and location changes, the National Conservatory of Music and Dance was opened by King Muhammad V on May 26, 1957.
Also in 1957, Cheqara – along with several friends – founded the Tétouan Conservatory Orchestra, to conserve and perform the music of Tetuan and Morocco. Later, Cheqara founded the Cheqara Orchestra of Tétuan.
Cheqara did much to popularize Andalusian music. Prior to the advent of Abdessadeq, Andalusian music was largely an elite music for Andalusians alone. Abdessadeq had a popular modern image and recorded with flamenco ensembles. In this way, he helped to create the image that Andalusian music was "hip."
Much of the Andalusian popular songs or Cha'abi (Sha'abi) are believed to have been appropriated from female Andalusian musicians of Tetuan such as Hajja Shili and Hajja Shahaba. Because of sexism, they were not permitted to record or perform if any males were present and are henceforth not well known. Reportedly Abdessadeq Chekara used to sit with Hajja Cha'haba and Hajja Shili and learn the women's songs, only to go on to record them. Many of the popular Andalusian songs (such as Ben't Bladi) are written from a women's perspective
Abdessadeq died on October 31, 1998, after a prolonged illness.
Noureddine Chekara, Abdessadeeq's son, has also been very instrumental in carrying on the family name. Noureddine played with his father Abdessadeq Cheqara in the ensemble since he was a young child, being the youngest member of the ensemble. He teaches violin (kamanja) and singing at the Tetuan Conservatory of Music since 1983. His innovative work in preserving and developing the Andalusian legacy continues with fellow Tetuani, [Tarik Banzi] Tarik Banzi of Al-Andalus ensemble or [[Radio Tarifa] 
Another ensemble is the Orquesta Chekara de Tetuán, based in Spain and under the guidance of Jallal Cheqara, a distant nephew of Abdessadeq. Since Jallal never performed in the Cheqara (Chekara) ensemble, nor did he study in the Tetuan Conservatory, the name of his ensemble has been controversed.