Sao Paulo is about 1.3 times smaller than Jacksonville.

Jacksonville (map shows its 197 named neighbourhoods; the area covers the whole city) is approximately 1,935 sq km, while Sao Paulo is approximately 1,523 sq km, making Sao Paulo 78.69% the size of Jacksonville.
Tip: This to-scale comparison of Jacksonville vs. Sao Paulo uses the Mercator projection, which distorts the size of regions near the poles.
Our free app, MapSize by MyLifeElsewhere — compare any two places, to scale on your mobile device.