Chicago is about 1.5 times smaller than Chesapeake.

Chesapeake is approximately 877 sq km, while Chicago is approximately 590 sq km, making Chicago 67.29% the size of Chesapeake.
Tip: This to-scale comparison of Chesapeake 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.