Azad was born as Chandrashekhar Tiwari on 23 July 1906 in Bhavra village, in the present-day Alirajpur district of Madhya Pradesh. His forefathers were from Badarka village near Kanpur (in present-day Unnao District). His mother, Jagrani Devi Tiwari, was the third wife of Sitaram Tiwari, whose previous wives had died young. After the birth of their first son, Sukhdev Tiwari, in Badarka, the family moved to Alirajpur State.

His mother wanted her son to be a great Sanskrit scholar and persuaded his father to send him to Kashi Vidyapeeth, Banaras, to study. In December 1921, when Mohandas K. Gandhi launched the Non-Cooperation Movement, Chandra Shekhar, then a 15-year-old student, joined. As a result, he was arrested. On being produced before a magistrate, he gave his name as "Azad" (The Free), his father's name as "Swatantrata" (Independence) and his residence as "Jail". From that day he came to be known as Chandra Shekhar Azad among the people.

Sindhal Bhil, son of Tantia Bhil, killed by an English officer Wattson was the first person who educated him about the importance of freedom of India. Which is considered as a major turning point of his views in chilhood. After suspension of the non-cooperation movement in 1922 by Gandhi, Azad became more aggressive. He met a young revolutionary, Pranvesh Chatterji, who introduced him to Ram Prasad Bismil who had formed the Hindustan Republican Association (HRA), a revolutionary organisation. Bismil was impressed by Azad, when Azad reportedly put his hand over a lamp and did not remove it till his skin burnt. He then became an active member of the HRA and started to collect funds for HRA. Most of the fund collection was through robberies of government property. He also wanted to build a new India based on socialist principles. He was involved in the Kakori Train Robbery of 1925, in the attempt to blow up the Viceroy's train in 1926, and at last the shooting of J.P. Saunders at Lahore in 1928 to avenge the killing of Lala Lajpat Rai.

The Hindustan Republican Association (HRA) was formed by Bismil, Chatterji, Sachindra Nath Sanyal and Shachindra Nath Bakshi in 1924. In the aftermath of the Kakori train robbery in 1925, the British clamped down on revolutionary activities. Prasad, Ashfaqulla Khan, Thakur Roshan Singh and Rajendra Nath Lahiri were sentenced to death for their participation. Azad, Keshab Chakravarthy and Murari Sharma evaded capture. Chandra Shekhar Azad later reorganized the HRA with the help of Revolutionaries like Sheo Verma and Mahaveer Singh. Azad was also a close associate of Bhagwati Charan Vohra who along with Bhagat Singh, Sukhdev, and Rajguru, helped him to transform the HRA into the HSRA in 1928 so as to achieve their primary aim of an independent India based on socialist principle. The insight of his revolutionary activities are described by Manmath Nath Gupt a fellow member of HSRA in his numerous writings. Gupta has also written his biography titled "Chandrashekhar Azad" and in his book History of the Indian Revolutionary Movement (English version of above: 1972) he gave a deep insight about the activities of Azad and the ideology of Azad and HSRA.

Starting from Manoj Kumar's 1965 film Shaheed, many films have featured the character of Azad. Sunny Deol portrayed Azad in the movie 23rd March 1931: Shaheed. In the movie The Legend of Bhagat Singh, starring Ajay Devgan, Azad was portrayed by Akhilendra Mishra.

The lives of Azad, Bhagat Singh, Rajguru, Bismil and Ashfaq were depicted in the 2006 film Rang De Basanti, with Aamir Khan portraying Azad. The movie, which draws parallels between the lives of young Revolutionaries such as Azad and Bhagat Singh, and today's youth, also dwells upon the lack of appreciation among today's Indian youth for the sacrifices made by these men.