Chicago is about 8 times bigger than Santa Ana.

Santa Ana (map shows its 60 named neighbourhoods; the area covers the whole city) is approximately 71 sq km, while Chicago is approximately 590 sq km, making Chicago 732% larger than Santa Ana.
Tip: This to-scale comparison of Santa Ana vs. Chicago 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.