This thesis analyzes the economics and financing of the recent purchases of the Indiana Toll Road and Chicago Skyway. Similar privatizations have been occurring around the world, but the economic motive for such transactions has been unclear. The analysis attempts to isolate the costs and benefits of such transactions as the transfer of the asset from public to private owner takes place. I examine whether the privatization would have been financially beneficial for the State of Indiana or the City of Chicago if it did not face budget constraints or political constraints on raising tolls. There seems to be significant disadvantage of such deals absent these constraints. I show this by computing value under various scenarios. After analyzing the results, I conclude by highlighting the policy implications for such privatization deals in future.