Boston is about 7 times smaller than Chesapeake.

Chesapeake is approximately 877 sq km, while Boston is approximately 124 sq km, making Boston 14.15% the size of Chesapeake.
Tip: This to-scale comparison of Chesapeake vs. Boston 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.