Chicago streets litter themselves
with sequins and vintage gin -
^^
I love the way you have used 'litter' in the first line. It really is a great way to open a poem with such detail, even though it is the first line you have set the location so well as well as the description of the sequins and vintage gin - words that have truly painted this scene!

chin-length bobs sway and
swing in unison with
jive turkey men.
^
Wow I feel like I am one of these men spinning with the music being played. Your words so compelling in nature as well as melded with the terminology of dance. 'Swing with unison' takes me back to times I have watched choreographed dance movies and how they all are in time and all robotically move together, so effective

Imperials camp amongst
a hundred-proof alleyway,
^^
You have set forth such description of the crowds watching that I can visually see it come to life, crowded alleyways, people so anxious to see the dancers, the streets filled with dizzying lights and the smell of gin scenting the atmosphere, the feeling for community as so many people join together!

chasing audacious flappers
for an after hours soiree.
^
What a way to end such a brilliantly written piece
I love your essence of sophistication - finding such words to embed smoothly thorough your writing providing more emphasis, flavour and power to your poem!

A great read!
5/5 from me