Cleveland is about 2.9 times smaller than Chicago.

Chicago is approximately 590 sq km, while Cleveland is approximately 201 sq km, making Cleveland 34.13% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Cleveland 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.