This paper aims to explore the issues faced by online booking users in the Indian market. Although it is easy and diverse, major issues include difficulty finding travel packages, poor customer support, and lack of local transportation arrangements. By exploring these challenges, this paper aims to investigate the challenges faced by users in the online travel booking market, despite its convenience and diversity, and guide improvements in these platforms, leading to more efficient services for travellers. In addition to the above challenges, another significant issue faced by users is the lack of transparent pricing. Often, users find that the final price at the time of payment is significantly higher than what was initially displayed. This is due to the addition of various hidden charges and fees, which leads to a poor user experience. Addressing this issue by providing clear, upfront pricing could greatly enhance user satisfaction and trust in online travel booking platforms. Moreover, users also report difficulties with understanding the terms and conditions of their bookings. This data is often long and filled with legal jargons, making them difficult to comprehend for the average user. This can lead to misunderstandings and disputes down the line. Simplifying these documents and making them easier to understand could go a long way in improving the user experience. Lastly, the lack of personalised recommendations based on past bookings or searches is another area where these platforms could potentially improve. By using data analysis and machine learning algorithms, these platforms could provide more personalised and relevant recommendations, thus improving user engagement and satisfaction.