Sarasota is about 15 times smaller than Chicago.

Chicago is approximately 590 sq km, while Sarasota (map shows its 40 named neighbourhoods; the area covers the whole city) is approximately 38 sq km, making Sarasota 6.46% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Sarasota uses the Mercator projection, which distorts the size of regions near the poles.
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