Charlottesville is about 22 times smaller than Chicago.

Chicago is approximately 590 sq km, while Charlottesville is approximately 27 sq km, making Charlottesville 4.5% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Charlottesville 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.