Chicago is about 2 times bigger than Fort Wayne.

Fort Wayne (map shows its 315 named neighbourhoods; the area covers the whole city) is approximately 289 sq km, while Chicago is approximately 590 sq km, making Chicago 104% larger than Fort Wayne.
Tip: This to-scale comparison of Fort Wayne 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.