Jackson is about 2 times smaller than Chicago.

Chicago is approximately 590 sq km, while Jackson (map shows its 125 named neighbourhoods; the area covers the whole city) is approximately 289 sq km, making Jackson 49.04% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Jackson 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.