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Pretty easily Chicagoland. It has a more tightly clustered core centered on the massive city of Chicago with some smaller surrounding offshoots. While DC/Baltimore are two separate cities that have sprawled into each other. Howard and Anne Arundel Counties really are suburbs of both cities. But, for the most part they each feel like their own place.
I'm surprised this was even brought up, but I guess CSA fanatics love to point to the numbers and try to compare apples to watermelons. I've only been to DC a couple of times, but at least for now, in no way does it feel as large (massive is a better adjective) as Chicagoland. I'm sure NYC makes Chicagoland feel a similar way.
Chicago area alone makes me feel like I'm in a bigger time area while the DC/Baltimore area is more suburban in feel.
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