Chicago is about 15 times bigger than Gisborne.

Gisborne (map shows its 10 named neighbourhoods; the area covers the whole city) is approximately 38 sq km, while Chicago is approximately 590 sq km, making Chicago 1,435% larger than Gisborne.
Tip: This to-scale comparison of Gisborne vs. Chicago uses the Mercator projection, which distorts the size of regions near the poles.
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