Cost of living: 53.4% above U.S. average Do you know the way to San Jose? It probably involves a stop at your bank for money. Silicon Valley's unofficial capital has placed fifth or sixth among America's most-expensive cities every year since CCER began releasing its annual list in 2008. That's mostly because San Jose housing costs 163.9% above the U.S. average. Zillow estimates the median San Jose home is worth $567,700, up 18.9% in just the past year. CCER also found that San Jose utilities run 26.6% above average, while groceries cost 21.4% more than most U.S. households pay. Similarly, health care runs 18.2% ahead of average, while transportation is 11.4% more than usual. If that's not enough to turn you off from moving there, Zillow has some 3,400 San Jose-area properties listed for sale.