Chakraborty was born in 1980 in Kolkata, India. She is the daughter of Chandana Chakraborty and the renowned Indian classical singer Ajoy Chakraborty. From the age of two she exhibited keen interest in music. She had accompanied her father in his world tours of music performances since late 1980s (She had sung her first song, a tarana, at age 7, at the Calcutta Rowing Club). At age ten, she started learning Indian classical music at the academy of Pandit Jnan Prakash Ghosh who was also her father's guru, later joined ITC Sangeet Research Academy from where she graduated in 2004, and was also groomed by her father. Vijay Kichlu, director of the academy fine tuned her skill in rendering Khayal. She also trained under her father at his Shrutinandan school of music in Kolkata. She has not only specialized in rendering of Khayals and Tumri but she has also learned South Indian Classical music from Balamurali Krishna from 2002. She completed her schooling at Patha Bhavan school, Kolkata. In 2002, she graduated from the Jogamaya Devi College, an affiliated undergraduate women's college of the University of Calcutta, in Kolkata with a first class degree in philosophy. She did her masters in philosophy from Jadavpur University, Kolkata, with top honours.
Chakraborty has participated in many major concerts. Apart from rendering Khyals in her performances she has also occasionally adopted contemporary form of Indian pop music. She performed at the Dover Lane Music Conference from the age of 20 and continued participating for the next 5 years. In her recitals she presents a mature and often with rhythmical swing succeeded by unrestrained taans in three and-a-half octaves. 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, morning raga Todi was rendered by Kaushiki; the song rendered was ‘Mori Naiyya Par Karo Re...’. Two other artists, Kalapini Komkali of the Gwalior gharana and Nandini Bedekar of the Jaipur-Atrauli gharana, also rendered songs in the same raga Todi at the same venue during the morning session. Bharat Kamat on the tabla and Suyog Kundalkar on the harmonium provided support to all three artists. 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, Ulhas Kashalkar, and Devaki Pandit. This rendering was a departure from the normal evening concerts, and the ragas were sung in time periods appropriate to each raga, starting from early morning till evening.
In the early stages of her career, in August 2003, Chakraborty gave a live performance in London which was released as the record "Pure". Her father had accompanied her on harmonium on this occasion. She also performed at the ITC Sangeet Sammelan in India, the Spring Festival of Music (California), Sawai Gandharva Bhimsen Sangeet Mahotsav and Parampara Program (Los Angeles). For her musical performances she has been acclaimed as "torchbearer of the Patiala tradition".
Chakraborty hosts a weekly talk-show with singers in the entertainment channel Ruposhi Bangla. The talk-show named "Gaan-Golpo ar Gaan" (Songs, Stories and Songs), aired on Sundays, presents music and gossip. She presents Bengali songs such as Classical, Rabindra Sangeet, Najrulgeeti, Folk music, Toppa, Adhunik, Bangla Bands, Film songs, and Remixes. Her guests who have appeared on this show Banasree Sengupta, Subhamita, Lopamudra Mitra and her husband music director Joy Sarkar, her father, Ajoy Chakraborty, as the guests.
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. The first programme of the group was planned to be held on 20 January 2015 at Kalamandir, Mumbai. Kaushiki was the vocalist and the other members of this group were Shaoni Talwalkar on the tabla, Mahima Upadhyay on the pakhwaj, Debopriya Chatterjee on flute, Nandini Shankar on the violin while the Kathak dance performance was to be performed by Bhakti Deshpande. They are daughters or grand daughters or disciples of famous Hindustani musicians. Chakraborty presented this musical ensemble with her group at the Carnegie Hall in October 2015; the programme was of 90 minutes duration.
Chakraborty has been the recipient of many awards. She received the Jadu Bhatta award in 1995, favourably mentioned and appreciated after her opening song at the 27th annual ITC Sangeet Sammelan in New Delhi in 1998, and received Outstanding Young Person in 2000. She received the BBC Award (2005) for outstanding achievement in music when she was 25 years old. 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". BBC also made a short film featuring her musical journey — which covered people and places linked with her music. She has also received Sangeet Natak Academy's Ustad Bismillah Khan Puraskar 2010 for Hindustani Vocal Music, and the 2013 Aditya Birla Kalakiran Puraskar.
Chakraborty married Parthasarathi Desikan, also a professional singer in Hindustani music, in 2004 and they have a son, Rishith.
Chakraborty's discography includes "Footsteps," a solo debut in 1998, and "A Journey Begins" (2002). Her album "Pure" in 2004 was a record of her performance in London on 30 August 2003. She has also sung a kirtan at MTV Coke Studio – Season 2 – song name – Lagi Lagi with Shantanu Moitra & Swanand Kirkire. Her other popular song recordings are for movies Water, Thirumanam Enum Nikkah(2014) and Kutti Puli (2013). 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. However, she appeared in only one song sequence in the film Chitrangada which sang herself. She has sung songs for movies, such as her first song for the film Chaplin, Teen Kanya, a Hindi song Rahoon tere peechhey for Paanch Adhyay, Gulaab Gang. About her performances she says: "But I never try to act like a 60-year-old because I’m not that. Superimposed seriousness would just be a thing of pretense, not me. I like to sit on stage and chat with my audience, not close my eyes and alienate myself."
Chakraborty has released her Audio Cd album titled "The Best of Kaushiki Chakraborty." Some of her other classical audio recordings are: Dhrupad Alap in Poorvi raga, Dhrupad in Poorvi raga, Khayal in Bageshree raga (in teen taal), Khayal in Bageshree raga (in ektaal), and Varnam in Swarashtram raga.