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(never noticed how dc resembles chi a little bit...)
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I think 14th Street specifically resembles Chicago because it's one of the few corridors in Washington where 3 story commercial buildings are the dominant character for a very long stretch, which is very Chicago-like.
It's worth noting that 14th Street really is not typical for Washington. Generally our retail streets are shorter and so continuous. Each neighborhood has its main street, which doesn't necessarily connect to the next neighborhood's main street. And those long commercial streets we do have (the state-named avenues specifically) often have enough apartments or offices mixed in that they don't have that same 3 story commercial character.
In the sense that Chicago is so full of retail streets that just go on for miles, DC really only has a couple of similar examples, and 14th Street is one of them.