Transportation planning requires more efforts from city planners to use rational techniques to determine optimum road routes. To fulfill this requirement, this study aims at generating the cheapest and the shortest scenario based routes using Geographic Information Systems (GIS) and Advanced Spaceborne Thermal Emission and Reflection Radiometer (ASTER) Digital Elevation Model (DEM) with Least Cost Path analysis between the Simav and the Kutahya cities, and comparing them with existing routes. For generating the shortest and the cheapest route, these cities are selected as sample since the study region is located in the transition area between central Anatolia and Aegean Region which has access to the sea and regional ports. The methodology used in this study is composed of three parts: first part consists of two steps; (i) generating the factors and (ii) determining scenarios focusing on different transportation themes that are used in the study process. In second part all factors are weighed regarding scenarios. In the third part of the study the outputs Path A (cheapest) and Path B (shortest) are generated by Least Cost Path analysis. The output routes were compared not only with each other, but also with the existing routes in terms of the generated factors.