4. Valparaiso
IM Score: 24
Rent Cost: $365
Hospital to Population Ratio: 94,876
Flight to U.S. Cost: $772
Quality of Urban Life Index Rank: 61
Festivals, street arts, and colorful architecture are all the things you can expect if you settle in Valparaiso. The nightlife is also considered great for Chilean standards, and if you like bars and nightclubs, you won’t be bored here. Besides the second lowest rent, the city also has the second lowest flight to U.S. cost on our list of best places to retire in Chile. The temperatures are a bit lower than in other places on our list, and you can expect occasional snow.