Chicago

I believe Chicago is the most distinctive American city.  The line "I'm writing this in a hotel room in Chicago" calls to mind images of a seedy dump with the letters -T-E-L flashing on a neon sign outside the window.  A gunshot from the street below, a woman's scream from the stairwell.  Actually ,of course, it's quite nice, like any decent chain hotel.

Certain philistines will say that honor goes to New Orleans, but in truth Chicago is more Chicago than New Orleans is New Orleans.  New Orleans is a city of music, but the Blues Brothers could never have been filmed there.  You need that great scene with Elwood and Jake in that seedy apartment with one L-Train after another going by outside.  Louis Armstrong was born in New Orleans, but he moved to Chicago.  

New Orleans has wonderful food, and in this one area may outshine even the mighty Chicago, but Chicago has its own distinct regional cuisine as well.

Chicago has a muscularity that New Orleans lacks.  Chicago says to you, "Get up and make something of the world!"  New Orleans says, in a genteel way, "Why bother?  Everything worth doing has already been done.  Meanwhile, have a muffaletta."  Even the famous political corruption is somehow admirable - it's ballsy, it speaks of wanting something and going after it.  It is impossible to imagine Carl Sandburg writing a poem about New Orleans:

They tell me you are wicked and I believe them, for I have seen your painted women under the gas lamps luring the farm boys.
And they tell me you are crooked and I answer: Yes, it is true I have seen the gunman kill and go free to kill again.
And they tell me you are brutal and my reply is: On the faces of women and children I have seen the marks of wanton hunger.
And having answered so I turn once more to those who sneer at this my city, and I give them back the sneer and say to them:
Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning.

Flinging magnetic curses amid the toil of piling job on job, here is a tall bold slugger set vivid against the  little soft cities...

Well, I can't do better than Sandburg, so I'll leave off here.