As a recent Chicago transplant I was initially struck by the similarities between Michigan Ave and its coastal counterparts -- 5th Ave and Rodeo Drive. Nearly a year of pounding the Mag Mile's pavement later, I can confidently say they share only storefronts.
Chicagoan's are the friendliest people I have encountered in any city. What Chicago lacks in attitude and excess, both characteristic of NYC and L.A., it makes up for in "Midwestern Charm" and sensible street style. The city's realistic take on trends is indicative of the laid-back Chicago lifestyle.
So what exactly is Chicago style? It's a refreshing blend of J.Crew and Urban Outfitters, with an emphasis on comfort and individuality. On any given day you will spot leather jackets and Burberry trenches alike. Of course, certain neighborhoods are more conservative (Lincoln Park) or casual (Wicker Park).
However, the city's street style can not be characterized by just one fashion genre: unlike D.C.'s prepsters, Brooklyn's hipsters, or Manhattan's fashion-forward glamazons.
While Chicago's women might have access to the most high end stores, you will not find them suffering (physically or financially) in the name of fashion. I admire the Chicago shopper's agenda -- the individual who wants to invest in practical purchases, and will actually enjoy wearing them.