Because each indoor site has its own radio propagation characteristics, a site survey process is essential to optimize a Wi-Fi ranging strategy for range-based positioning solutions. This paper studies an unsupervised learning technique that autonomously investigates the characteristics of the surrounding environment using sensor data accumulated while users use a positioning application. Using the collected sensor data, the device trajectory can be regenerated, and a Wi-Fi ranging module is trained to make the shape of the estimated trajectory using Wi-Fi similar to that obtained from sensors. In this process, the ranging module learns the way to identify the channel conditions from each Wi-Fi access point (AP) and produce ranging results accordingly. Furthermore, we collect the channel state information (CSI) from beacon frames and evaluate the benefit of using CSI in addition to received signal strength (RSS) measurements. When CSI is available, the ranging module can identify more diverse channel conditions from each AP, and thus more precise positioning results can be achieved. The effectiveness of the proposed learning technique is verified using a real-time positioning application implemented on a PC platform.