Chicago is about 2.1 times smaller than Nashville.

Nashville (map shows its 91 named neighbourhoods; the area covers the whole city) is approximately 1,232 sq km, while Chicago is approximately 590 sq km, making Chicago 47.89% the size of Nashville.
Tip: This to-scale comparison of Nashville vs. Chicago uses the Mercator projection, which distorts the size of regions near the poles.
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