Madrid is about 1.4 times smaller than Chesapeake.

Chesapeake is approximately 877 sq km, while Madrid is approximately 604 sq km, making Madrid 68.94% the size of Chesapeake.
Tip: This to-scale comparison of Chesapeake vs. Madrid 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.