Chicago is about 12 times bigger than New Haven.

New Haven is approximately 48 sq km, while Chicago is approximately 590 sq km, making Chicago 1,118% larger than New Haven.
Tip: This to-scale comparison of New Haven 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.