Milwaukee is about 1.2 times smaller than Jackson.

Jackson (map shows its 125 named neighbourhoods; the area covers the whole city) is approximately 289 sq km, while Milwaukee is approximately 249 sq km, making Milwaukee 86.11% the size of Jackson.
Tip: This to-scale comparison of Jackson vs. Milwaukee 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.