Tokyo is about 2.9 times bigger than Madison.

Madison (map shows its 124 named neighbourhoods; the area covers the whole city) is approximately 217 sq km, while Tokyo is approximately 619 sq km, making Tokyo 186% larger than Madison.
Tip: This to-scale comparison of Madison vs. Tokyo 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.