It's Always Winter But Never Christmas
Having never lived in the Southern Hemisphere before, the biggest adjustment for me has been accepting the fact that in the middle of the "summer months" of June, July and August, we expats down in Chile are subject to freezing temperatures without the perks of snow and Christmas. Not cool, Chile. Not cool.
That being said, and having lived in Indiana for several years now, I have to confess that it really doesn't get THAT cold in Santiago. Most days are in the 50's or 60's and overcast, with lows getting down into the 30's at night (tonight the low is expected to be 25 degrees Farhenheit, which is the lowest I've seen it all winter). Every now and again we'll get lucky: the sun will come out, bringing the "winter" temperature up closer to the 70's, and really quite pleasant.
So, to be honest, the outside world doesn't get too cold in Santiago, even in the winter.
...But INSIDE your apartment will be a whole different story!
Heating is not very common in Chile, and if you can get you will be paying a pretty penny. Unfortunately, Chile asn't quite latched on to the idea of well-insulated windows either. The result is that often times, your the temperature in your apartment will feel much, much, colder than the outdoors. So, on evenings like this one, with lows below freezing, I am to be found in my apartment, invariably bundled up and drinking hot tea like it's going out of style.