Wellington is about 1.3 times smaller than Chicago.

Chicago is approximately 590 sq km, while Wellington (map shows its 57 named neighbourhoods; the area covers the whole city) is approximately 444 sq km, making Wellington 75.28% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Wellington 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.