Chicago is around the same size as Colorado Springs.

Colorado Springs (map shows its 11 named neighbourhoods; the area covers the whole city) is approximately 523 sq km, while Chicago is approximately 590 sq km, making Chicago 13% larger than Colorado Springs.
Tip: This to-scale comparison of Colorado Springs 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.