Adoption of any new technology in an organization is a crucial decision as it can have its impact at technical, economical, and organizational level. One of such decisions is related to adoption of Cloud-based services in an organization. Cloud Computing provides elastic resources as per the demand and provides the facility to pay as per the use. Thus, it is changing the way IT infrastructure is used today with huge benefit of cost savings. However, if the solution adopted by an organization is not fulfilling the requirements, it can have tremendous negative consequences at technical, economical, and organizational level. Therefore, the decision to adopt Cloud-based services should be based on a methodology that supports a wide array of criteria for evaluating the available alternatives. Also, as these criteria or factors can be mutually interdependent and conflicting, a trade-offs-based methodology is needed to make such decisions. This paper, therefore, discusses the design, implementation, and evaluation of the prototype developed for automating the theoretical methodology of Trade-offs based Methodology for Adoption of Cloud-based Services (TrAdeCIS) developed in (Garg and Stiller, 2014). This system is based on Multi-attribute Decision Algorithms (MADA), which selects the best alternative, based on the priorities of criteria of decision maker. In addition the applicability of this methodology to the adoption of cloud-based services in an organization is validated with several use-cases towards the end of the paper. Furthermore, the extendibility of this system to other domains is being evaluated with respect to Train Operating Companies, who wish to find out the best alternative of providing Internet connectivity and voice calls on-board trains.