Chile gets five stars, Santiago gets none.
While I generally liked Chile I did not like Santiago. It was an unattractive city and most neighborhoods seemed to be very seedy. I work for an airline and travel the world and Santiago is one of the few cities I would not like to revisit. On the other hand, Puerto Montt (about a two hour flight south of Santiago) is a gem and seems to be off the beaten tourist track. From there, we rented a car and took the ferry to Chiloe island. It was the highlight of the trip and something I'll always remember.
The Chilean people are great but if you're travelling independently you'd better know at least a little Spanish.