Madison is about 2.9 times smaller than Tokyo.

Tokyo is approximately 619 sq km, while Madison (map shows its 124 named neighbourhoods; the area covers the whole city) is approximately 217 sq km, making Madison 34.99% the size of Tokyo.
Tip: This to-scale comparison of Tokyo vs. Madison 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.