Despite the general thought of Santiago as a dirty, horrible, polluted and boring city, which is true sometimes, I love to live here. I really do, and believe me, I have live in better places.
Santiago worth it, specially to visitors I think. I know that Americans are always amazed of the mountains sorrounding the city, and I can’t believe how locals aren’t! I mean look at the Cordillera in winter, full of snow, and in summer, with all the shades of colors it has…and it’s only one part of the good things the city has. Downtown is great. El Parque Forestal is nice, cool and always full of things to do; Lastarria street is incredible, as well the Palacio de la Moneda, specially with the new gallery beneath it. Even the “folk” places like La Vega or Patronato or Paseo Ahumada are fun. Santiago is improving every year; new and exciting cultural things are developing, is getting cleaner, nicer…I recommend it, I really do.
Where I would go? Downtown, first (Cerro Santa Lucia and all those places). If is winter, to the skiing centers. Summer, to the hills sorrounding the city, or to the Cajon del Maipo, Maipo river is beautiful. To the museums, some are not very known but great (like the Militar Museum). To Mercado Central (good food). Some places in the “rich” part are cool too, Vitacura is nice. Just…wander around, it worth it!
Of course, Chile it self is not Santiago, go south :P