Chicago is about 51 times smaller than Lesotho.

Lesotho is approximately 30,355 sq km, while Chicago is approximately 590 sq km, making Chicago 1.94% the size of Lesotho.
Tip: This to-scale comparison of Lesotho vs. Chicago 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.