The 20 most expensive places to rent Rank City $/sq. ft* Rank City $/sq. ft* 1 New York $26.04 11 San Diego $19.19 2 Boston $24.33 12 Oakland, Calif. $17.66 3 Honolulu $23.27 13 Washington, D.C. $17.54 4 San Francisco $22.48 14 Central New Jersey $16.54 5 N. New Jersey $22.35 15 Philadelphia $15.40 6 Stamford, Conn. $21.76 16 Riverside-San Bernardino, Calif. $14.81 7 Nassau-Suffolk, N.Y. $21.05 17 Baltimore $13.91 8 Los Angeles $20.34 18 Chicago $13.57 9 San Jose, Calif. $20.23 19 Miami $13.49 10 Orange County, Calif. $19.54 20 Sacramento, Calif. $13.16 Source: National Real Estate Index *Price for ‘Class A’ apartment, top quality buildings maintained well