Chicago is about 1.3 times bigger than Wellington.

Wellington (map shows its 57 named neighbourhoods; the area covers the whole city) is approximately 444 sq km, while Chicago is approximately 590 sq km, making Chicago 33% larger than Wellington.
Tip: This to-scale comparison of Wellington 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.