I personally am a HUGE fan of fried empanadas. My favorite is cheese, though I love seafood ones too. Shannon was asking for recommendations for a trip to the 5th region and all that could really come to mind is all the places that sell greasy cheesy food!
So here are my top recommendations for fried empanadas, not in any significant order:
Cafe Journal [Viña del Mar, corner of Agua Santa/Alvarez] - This restaurant/bar is a huge attraction especially for gringos, and turns into a club atmosphere some nights. Its owned by a German family, is decorated nicely, has 2 floors and a great outdoor patio, an amazing selection of drinks. Prices are generally above average but not extraordinary (Ex: a daquiri or the like costs ~2,500). The wonderful thing is that you can order the empanadas until well into the night(/morning), and a cheese empanada costs only 600 pesos. 99% of the time they are super fresh with melty, burn-your-tongue cheese.
Horcon- [I'm cheating. Horcon is a city but you can't go wrong] - Take your pick, this little seaside city is full of excellent empanada shops in the medium price range. The city is about an hour bus ride from Viña de Mar, is great for a day trip or an overnight. Its a little fisherman's village with nice beaches (famous for the "nudist" one). Pick up the bus on Av. Libertad, the plaza Viña, or Alvarez in Viña, Avenida España, or Errazuriz in Valpo. It'll say Horcon on the front.
Entre masas [Viña del Mar - Cinco Norte 377] This is one of many tiny shops offering empanadas in the maze of ponientes/nortes in Viña. Prices are a little high with most of the 20+ varieties costing around or over 1,000 each. However, they are fresh and delicious. Better in summer as the area is much more vibrant.
___[edit: Empanadas Varieta]________ I seriously blanked on the name. I'll edit this post when it comes back to me. [Viña del Mar - 2 Norte con Quillota]. They offer a zillion flavors, a cute sit down area similar to something pleasing in the US like a Panara Bread shop, freshly fried, etc... I have sometimes found mine to be almost too fried, but then again I'm the type of person that doesnt like crust. Again expect to spend around mil pesos per empanada. Or walk up the street as calle Quillota is like one big empanada fair.
Las Deliciosas [Concon - right off the traffic circle] These empanadas are the gooey greasy bundle of cheese+ you've been waiting for all your life. They're cheaper than many of their Viña competitors with a cheese empanada costing around 600 pesos, though the restaurant is less cute and personal. However, I have heard a story of an empanada not sitting well there, so maybe with care comes quality.
Empanadas famosas [Valparaiso - Salvador Donoso 1381, close off Bellavista and easy to miss]- Medium priced empanadas with lots of options and a high pass on the tasty factor. Accompanying Chileans have claimed they cook with dog meat but I'm willing to selfishly risk thats either an urban legend or a freaky story from long ago that will never affect my cheese or seafood empanadas. Still, they have kinda restrictive hours and frankly I haven't even seen them open in a while. Anyway they stay on my list.
My house- [Valparaiso] My boyfriend makes some great empanadas, specialty: cheese, tomato, mushroom, oregano, without lard (Yeah, manteca is lard, it sounds SO much less savory in English), and I fry them with very little burn on the crust and minimal kitchen injuries. Usually if everybody chips in for the ingredients its possible to convince him. :) Let me know if you're in town and want to meet up.
What am I missing? Feel free to recommend another for me or anybody else who stumbles across this.
[additional comment added January 17, 2012:
A Destajo in Valparaiso makes a GREAT oven baked vegetarian empanada for 800 pesos (and counting! haha). Its got cheese, a black olive, zucchini... and some other stuff. I'll have to go buy one to do further research!
They have two locations in Valparaiso, in Subida Cumming #55 and Subida Ecuador #6. Both locations are very centrally located and it's the type of place where you either stand around and eat the empanadas there or get it to go. ]