San Francisco. Very easy. SF plus 7 municipalities on East Bay:
------------------------- Population 1950 ------ Area ------- Density
Code:
New York ------- 10,244,422 -- 1,255 km² ---- 8,160 inh./km²
Chicago --------- 3,930,506 ---- 670 km² ---- 5,863 inh./km²
Los Angeles ----- 3,512,434 -- 1,502 km² ---- 2,339 inh./km²
Detroit --------- 2,048,410 ---- 414 km² ---- 4,951 inh./km²
San Francisco --- 1,386,789 ---- 342 km² ---- 4,053 inh./km²
Montreal -------- 1,164,133 ---- 164 km² ---- 7,098 inh./km²
Cleveland ------- 1,082,067 ---- 245 km² ---- 4,544 inh./km²
St. Louis ------- 1,044,363 ---- 233 km² ---- 4,486 inh./km²
Pittsburgh ------ 1,038,137 ---- 263 km² ---- 3,940 inh./km²
Toronto ----------- 889,869 ---- 142 km² ---- 6,267 inh./km²
Cincinnati -------- 708,469 ---- 256 km² ---- 2,768 inh./km²
Milwaukee --------- 637,392 ---- 129 km² ---- 4,922 inh./km²
Buffalo ----------- 600,198 ---- 108 km² ---- 5,394 inh./km²
Those numbers show how California went from the least dense urbanized areas in the world to the densest in North America.