I live in Chile, so I do have a few ideas for you. In Santiago: Cerro Santia Lucia and the craft market nearby. Cerro San Cristobal and the view from the top. You can either walk up and down or take an old side elevator. Barrio Lastarria near downtown. It's an old, cmlassic style neighborhood with nice cafes, bars, and a foreign movie theatre. The area of Providencia is nice to stay because it is safe and relatively close to everything else.
Around Santiago: Laguna Verde, Isla Negra and Pablo Neruda's house, Cajon del Maipo--the mouth of the river and the beginning of the Andes.
Viña del Mar-- a beautiful coastal city about 1.5 by bus from Santiago. Valparaíso-- Viña's artsier, bohemian costal twin.
In the South, Puerto Varas and Peurto Montt. in the North, La Serena and San Pedro de Atacama.
Any particular region you have a question about? Chile is a long country! about 6 years ago
Enterprise away from the airport and order it online , do not do a walk in. Airports have to add on extra taxes and fees. Enterprise will come pick you up for free. Just take a free hotel or parking airport shuttle away from the airport and have them come get you. Its a little work but will save you over 100 dollars. about 6 years ago
Once we head a 7 days journey to Chile. Apart of Concha Y Toro wineyard nearby Santiago and Vina del Mar mentioned above we managed to visit also Easter Island and Patagonia with Terra del Fuego. Here is good local tour operator http://www.cocha.com/ibe/common/home.do
Dream about nest journey with Atacama Desert and Torre del Pain National Park about 6 years ago