City size comparison

compared to

Chicago is about 2.9 times bigger than Oakland.

Oakland (map shows its 131 named neighbourhoods; the area covers the whole city) is approximately 202 sq km, while Chicago is approximately 590 sq km, making Chicago 192% larger than Oakland.
Tip: This to-scale comparison of Oakland vs. Chicago uses the Mercator projection, which distorts the size of regions near the poles.
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Compare further: Chicago vs. Oakland

Flip Comparison · See true size
See Chicago on top of Oakland
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Cost of Living Comparison · 7 categories - 2026 data
Oakland is 15.2% more expensive than Chicago
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