Madison is about 1.8 times bigger than San Francisco.

San Francisco (including the city proper only) is approximately 121 sq km, while Madison (map shows its 124 named neighbourhoods; the area covers the whole city) is approximately 217 sq km, making Madison 79% larger than San Francisco.
Tip: This to-scale comparison of San Francisco vs. Madison uses the Mercator projection, which distorts the size of regions near the poles.
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