Pittsburgh is about 4.1 times smaller than Chicago.

Chicago is approximately 590 sq km, while Pittsburgh is approximately 143 sq km, making Pittsburgh 24.32% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Pittsburgh 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.