Chicago is about 4.1 times bigger than Pittsburgh.

Pittsburgh is approximately 143 sq km, while Chicago is approximately 590 sq km, making Chicago 311% larger than Pittsburgh.
Tip: This to-scale comparison of Pittsburgh 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.