Milan is about 1.5 times bigger than San Francisco.

San Francisco (including the city proper only) is approximately 121 sq km, while Milan is approximately 182 sq km, making Milan 50% larger than San Francisco.
Tip: This to-scale comparison of San Francisco vs. Milan 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.