Homelessness is a complex and persistent issue in urban areas, with many different factors contributing to the experience of homelessness. As per the estimates of the United Nations, there are about 1.6 billion homeless people all around the globe with another 15 million being evicted forcibly each year. In India, the number of homeless people is estimated to be in the range of 1.77 million to over 18 million individuals. This problem is common in all countries despite their economic status being rich or poor. Living on the streets for a long time leads to dejection, despair, and hopelessness for a better and safer future. With no universally accepted definition, understanding and elimination of homelessness remain a Herculean task worldwide. This chapter investigates the social, economic, and administrative challenges faced by the homeless population in the planned city of Chandigarh, one of the most progressive capital cities of India. To attain the objectives of the study, data from 450 homeless respondents was collected based on mixed-method research and analysed using appropriate statistical techniques. The study found that lack of education remained one of the major driving factors behind homelessness along with the adverse impact of the Covid-19 pandemic. Lack of support and initiatives from the government had led to a strong feeling of despair and hopelessness among the homeless people occupying vacant plots in the Industrial Area Phase I, while another group of homeless people living in Sector 25 who had received some help from the government were hopeful for the continued support in future as well. The care dimension of the solidarity approach has been explored to provide long-term and sustainable solutions to the problem faced by the homeless population there. By caring for this homeless population, not only their socioeconomic conditions can be improved but even social integration can be strengthened by overcoming the economic, regional, and racial barriers. Based on the experiences of the respondents and the lack of success of various housing schemes launched by the government, the study proposes a ‘Housing for Work Scheme’ to effectively address the problem of homelessness in Chandigarh. By initiating the scheme which provides housing as well as employment opportunities for the homeless people on one hand and revenue generation for the Chandigarh administration on the other hand, it will be a win-win situation for all.