Chicago is about 8 times smaller than Auckland.

Auckland is approximately 4,894 sq km, while Chicago is approximately 590 sq km, making Chicago 12.05% the size of Auckland.
Tip: This to-scale comparison of Auckland 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.