Chicago is about 1.4 times smaller than Calgary.

Calgary (map shows its 242 named neighbourhoods; the area covers the whole city) is approximately 826 sq km, while Chicago is approximately 590 sq km, making Chicago 71.44% the size of Calgary.
Tip: This to-scale comparison of Calgary 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.