Like any country, Chile has is wonderful places and its awful slums, its points of magnificence and its filth. Here is a quick overview. Since I have been to nearly every place in Chile (at least on the list below other than those in the 11th region), I hope I can speak with some authority! You will probably need to have your map handy or look at the one scanned and posted here in late August.

Beautiful Places
1. Anywhere in the mountains, especially the Andes range.
2. Cities of Puerto Natales, Iquique and Arica beaches, and anywhere in the list below under spectacular scenery. 
3. Fifth region beach areas like Reñaca (Viña del Mar) and Algarobo.
4. Countryside and beach areas around Concepción.
5. La Serena
6. Just about any rural coastline, lake shoreline, or coastal range with an ocean inlet or a glacier.
7. Lago Chungará in the 15th region on the Bolivian border
Spectacular scenery (you should visit everything on this list)
1. Torres del Paine: Arguably the most beautiful place in the world, a couple hours north of Puerto Natales in the 12th region. Close second is Lago General Carrera, especially the southeast corner.
2. Lago Todo los Santos (or Lago Esmeralda, so-called for its emerald green water due to glacial runoff not allowing green light to refract): 10th region near Ensenada and just over an hour’s drive from Puerto Varas. Take the cruise across the lake, eat lunch, and cruise through Argentina too.
3. Zapallar: one of the most beautiful coastal range beach areas in the world. It rivals Santa Barbara. In the 5th region.
4. Puerto Varas, Frutillar, and Puerto Octay around Lago Llanquihue in the 10th region.
5. Siete Tazas in the 7th Region mountains.
6. Panguipulli and Puerto Fuy (14th region)
7. Pucón (9th region)
8. Lonquimay (8th region)
9. Easter Island
10. Lago Ranco (14th region)
Busting 1st World city: northeast Santiago
1. Las Condes
2. Vitacura
3. Lo Barnechea
4. Providencia
5. La Reina, Ñuñoa and Huecheraba (in certain parts)
Busting agricultural centers
1. Curicó and Talca (7th region)
2. San Fernando (6th region)
3. Rancagua–a bit run down though (6th region)
4. Los Andes and San Felipe in the 5th region.
5. Parral (7th Region)
6. Traiguen (9th Region)
Hideouts to get away from it all–literally–and never be seen or heard from again!
1. Hornopirén in the 10th region
2. Caleta Cortel in the 11th region
3. Chaitén in the 10th region (just had an eruption)
4. Quellón and/or Queilen in the 10th region
5. Cerro Castillo in the 12th region
6. Cerro Sombrero in the 12th region
7. Mamiña in the 1st region
8. Pica in the 1st region
9. Antuco in the 8th region
10. Just about any rural beach, desert, or mountain area at least 100 road miles from any significant urban center.
11. San Félix in the 3rd Region
Best places to live in Chile
1. Northeastern Santiago, if you like cities, excitement, activism and little difference from your present life in the First World. Schools, hospitals, and airline service are all top-of-the-line.
2. In any of the nice little cities around the lakes in the 9th, 10th, and 14th regions.
3. Along the coast in Viña del Mar, Con Con, Zapallar, La Serena, Iquique, or Arica.
4. If you want to pay almost no taxes and you are retired, choose Arica, Iquique, Punta Arenas, or Puerto Natales or a seasonal home for the summer in one of the latter two and a rest-of-the-year home up north in Arica or Iquique.
Best weather in Chile
1. Iquique and Arica are best if you hate rain and don’t mind living with zero rain and no plant life, along with temperatures constantly in the 50 to 80 degree range. Arica does have underground water at least and some irrigated areas. Iquique has sand and rocks.
2. Any of the nice little cities around the lakes in the 9th, 10th, and 14th regions are best if you like seasons, but no snow (other than in the mountains), can handle ample rainfall, and do not mind wearing a sweater or at least a light jacket eight months out of the year.
3. If you like a hot, dry summer and a foggy season the rest of the year, you might pick the valley between Rancagua and Osorno (the latter being the foggiest city in Chile).
Second World but quaint and growing little cities under 250,000 population
1. Osorno
2. Arica
3. Valdivia
4. Temuco (Indian center: probably too big for this list but does not fit well anywhere else)
5. Castro
6. Ancud
7. Los Ángeles
8. Chillán
9. Linares
10. Vallenar
11. Villa Alemana and Quilpué
12. Copiapó
Remote and lonely
1. Porvenir
2. Puerto Williams
3. Punta Arenas (but the history is rich and interesting and the food is great!)
4. Putre
5. Pozo Almonte
6. Colchane
7. Coihaique and the rest of the 11th region
8. San Pedro de Atacama
9. Ollagüe
10. Visviri
Run down and dilapidated (other than the small, nice, new neighborhoods)
1. Concepción (8th region)
2. Puerto Montt (10th region)
3. Valparaíso (5th region)
4. Talca (7th region)
5. Tocopilla (2nd region)
6. Antofagasta (2nd region)
7. Coquimbo (4th region)
Urban blight
1. The trash-laden road between Iquique and Pozo Almonte
2. Any one of a dozen slums around Santiago, especially just north and south of downtown
3. Ditto for Antofagasta, Concepción, and Valparaíso (ugly ports)
4. San Antonio (another ugly port)
Industry: unsightly and foul-smelling
1. Calama (next to Chile major copper strip mine in the 2nd region).
2. Talcahuana (with fish meal plant just north of Concepción)
3. Industrial areas of Santiago
4. Quintero (and anything near it) in the 5th Region, also much between San Antonio and Algarrobo
5. North side of Antofagasta