Valparaiso, Chile is the capital of cool - the rooftop views and vibrant energy gave me that unique sense of being in a faraway place. With maybe the best street art in the world, it fascinates me that the city isn't more well known.
Part of this reason may be due to logistics. While many cruises stop in the port there, in general few U.S. travelers make it to Santiago, let alone another 90+ minutes on the road west to Valparaiso. To read more about the road journey there and other Valparaiso travel tips, I recommend reading this post.
To get there, the best mile redemptions for U.S. residents are to Santiago using American, United or Delta (and their respective partners). 60,000 American or United miles, or 75,000 Delta miles, will get you a round-trip ticket in economy, or 100,000, 110,000, or 125,000, respectively, in business class. Expect $5 to $120 in booking fees.