Chicago is about 1.2 times smaller than Tehran.

Tehran is approximately 686 sq km, while Chicago is approximately 590 sq km, making Chicago 85.98% the size of Tehran.
Tip: This to-scale comparison of Tehran 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.