Anguilla is about 6 times smaller than Chicago.

Chicago is approximately 590 sq km, while Anguilla is approximately 91 sq km, making Anguilla 15.43% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Anguilla 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.