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All the city comparison threads happened on CITY VS CITY years ago, when people who were actually knowledgeable about these things frequented that board.
However, the lid on that coffin has slammed shut and the nails have been driven in. The intelligent people have all left, leaving behind only the idiots. Every dog has its day. :-)
Therefore, make good use of the Advanced Search feature if you're interested in real information.
Chicago's not directly in the flight path of DC to SF, but it's pretty close and it's a pretty great city. Milwaukee, I think, is closer to the flight path but it's a bit smaller.
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Detailed information about all U.S. cities, counties, and zip codes on our site: City-data.com.