I am planning a trip starting from Boston, and along the fringe of great lakes and get to Chicago. After that, I am going to down the Mississippi river and aim at New Orleans. Then I will turn west along the border with Mexico and pass Phenix to LA, the last stop will be San Francisco. My major interest are the cities on the route, and want to finish in one month.
Do you think it is realistic? how much do you estimate if I can find four person together with a car? or any other suggestions about this general plan? like interesting place along the great lakes, in Mississippi watershed or Arizona and New Mexico desert?