Chile is on my own personal list since word has it that it is home to one of the highest roads in the world (which I plan to skate at some point). That said its usually exorbitantly expensive to get down there, though it is relatively in-expensive to stay / eat etc once you have arrived.
$250 R/T is absolutely nuts, clearly a mistake and clearly won't last long.
Chile has a vibrant riding culture and some of the best skiing and snowboarding I have ever had the opportunity to partake in (so good that I left high school a little ... early... to get in on it.)
These fares will get you there during the southern hemisphere summer (no snow), so you are going to have to make due with Surfing and Skateboarding (Downhill or otherwise).
Downhill / Longboard
Chile is at roughly the same latitude as California (just opposite seasons) so a lot of the weather conditions are similar.
The roads are pretty much out of this world.
In my experience the locals are friendly, and everyone knows how to have a good time... plan on minimal sleep.
Yeah, there are waves too.
Waves. Lots of waves. Why am I not there right now.
This one is going to be here and gone fast (maybe by the time I finish writing it up), going out via text to Ams and Pros and Brands right....NOW. Get on it and let us know how it was when you get back.