I don’t know much about the skiing/snowboarding in Chile, but can tell you Portillo is beautiful. If you end up staying in Santiago a day trip out to Vina del Mar might be worth it too! It’s a $4.00 bus ride there and is about 2 hours and right on the ocean with amazing views of the ocean and clubbing in Valparaiso! In terms of traveling about the country, air- LanChile, would be the fastest, but most expensive option. I personally LOVED the bus system in Chile. Tur-Bus will take you pretty much anywhere for very good prices! Though, since Chile is so long it can take quite awhile to get anywhere-about 15-17 hours from Santiago to Puerto Montt/Chiloe region, but it’s a night bus trip and really comfortable and economic! I hope this helps some! Let me know if you want more details on anything