Chicago is about 4.7 times bigger than Salem.

Salem (map shows its 1 named neighbourhoods; the area covers the whole city) is approximately 127 sq km, while Chicago is approximately 590 sq km, making Chicago 365% larger than Salem.
Tip: This to-scale comparison of Salem 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.