[1] At age ten, she started learning Indian classical music at the academy of Jnan Prakash Ghosh who was also her father's guru.

Later, she joined the ITC Sangeet Research Academy from where she graduated in 2004,[2][3][4] and was also groomed by her father at his Shrutinandan school of music in Kolkata.

[5] In the two-day celebration in honour of vocalist Kishori Amonkar in recognition of her 60 years contribution to music held at Pune on 14 February 2011, Chakraborty rendered raga Todi.

Kumar Gandharva and Nandini Bedekar of the Jaipur-Atrauli gharana, also rendered bandishes in the same raga at the same venue during the morning session.

[8] In the unique musical sessions organized by Mumbai's National Centre for the Performing Arts (NCPA), ragas in different time-cycles were presented on 18 September 2011 by three vocalists which included Kaushiki Chakraborty, Ulhas Kashalkar, and Devaki Pandit.

[9] In the early stages of her career, in August 2003, Chakraborty gave a live performance in London which was released as the record "Pure".

[12] Chakraborty has formed an exclusive women's musical group called the "Sakhi" (meaning, friend) which is a forerunner in classical music in the country to "celebrate womanhood" and as a dedication to the famous mythological and historical woman of India – Ganga, Saraswati, Durga, Lakshmi, Draupadi, Kunti, Sita, Radha and Meera.

Chakraborty was the vocalist and the other members of this group were Shaoni Talwalkar on the tabla, Mahima Upadhyay on the pakhwaj, Debopriya Chatterjee on the flute, Nandini Shankar on the violin while the Kathak dance performance was by Bhakti Deshpande.

On receiving this award she was praised "as one of the brightest emerging artists in Indian vocal music" and as critic Ken Hunt said "we are talking superlatives".

[15] Rituparno Ghosh had asked her father to permit Chakraborty to act in his films but he refused saying that it would interfere with her musical career.

"[1] Kaushiki Chakraborty curated and presented the event- Remembering the Divas- at- The Nita Mukesh Ambani Cultural Centre- on March 31, 2024, along with other Indian Classical Singers, including Aruna Sairam.

Subbulakshmi, Shobha Gurtu, Noor Jahan, Kishori Amonkar[16][17] Chakraborty, along with Shreya Ghoshal, Sonu Nigam, Shankar Mahadevan, and Hariharan performed at Anant Ambani and Radhika Merchant's wedding in 2024.