Digital technology is instrumental in driving social transformations in areas such as the economy, politics, culture, and religion. An attempt was made in this present study to analyse the ground reality of Rural and Urban areas in the field of digitalization and digital practices in Tamilnadu, India. It is necessary to promote digitalized practices in Urban areas since its deliberately intertwined with business or economic activities. Apart from such factors the educational, political and legal aspects are seeking the direct interventions with digital world. In contrast the digitalization has been still growing and yet to be improved in rural areas according to its need. The study is based on qualitative in nature by employing the tools such as interviews schedule, case studies, and participant observation and hence, seeking the comparative analysis between a selected Urban area of Chennai region and a selected rural area in the outskirts of Chenni. India has been part of the digital society since the beginning of the 21st century with the introduction of the Internet and information and communication technology. People's every move and behavior in a digital society are calculated and recorded as data. In this global context of a digital society, India has created opportunities for digitalization for its people since 2000, with significant strides made between 2015 and 2016. Reliance Jio, a telecom company, helped to accelerate this process by offering free unlimited Internet packages on a mass scale. This led to a tremendous surge in service industries and the emergence of new sectors, as well as a digital revolution in the conventional systems of the economy, politics, culture, education, religion, and law. However, this transformation has also exposed a significant challenge namely the digital divide or digital inequalities. The study revealed that the prevailing socio-economic divide is the source of its wide digital divide. This digital divide exists across both rural and urban areas, affecting access to digital education and economic opportunities. The digital divide is also found between under-resourced urban areas and affluent residential areas. This comparative study exclusively brings out the equality and inequality aspects in both rural and urban polarities with respect to the digitalization.