The objective of this research is to explore the diverse challenges faced by the customer as well transport providers through the selected modes of transportation of the second most populous country in the world – India. Two separate well-structured questionnaires administered to garner the opinions on different challenges. A random sample of 100 equally selected from the customers of 3 modes of transportation along with 30 transport providers. The collected data was analyzed in Microsoft Excel and R Studio platforms using Percentile Rank Tool and R Programming Language for Chi-square test respectively. Traffic congestion coupled with parking is the major problem in case of roadways while Safety and cleanliness in railways are the first amongst the problems to reckon with. High fares and lack of trained employees are the biggest challenges faced by aviation industry. The research is concentrated only in the states of Andhra Pradesh and Telangana in India with most widely used three modes of transportation viz., Road, Rail and Airways. This research paper is first of its kind which has collected the opinions of both customers as well transport providers on the problems faced. This research proffers information about the challenges faced by the customers which there will be an enormous possibility to review their strategies and plans.