Milan is about 1.9 times smaller than Portland.

Portland is approximately 346 sq km, while Milan is approximately 182 sq km, making Milan 52.57% the size of Portland.
Tip: This to-scale comparison of Portland 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.