Vancouver is about 4.7 times smaller than Chicago.

Chicago is approximately 590 sq km, while Vancouver (map shows its 61 named neighbourhoods; the area covers the whole city) is approximately 126 sq km, making Vancouver 21.43% the size of Chicago.
Tip: This to-scale comparison of Chicago vs. Vancouver 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.