The irrepressible Manolo is infesting Chicago and about to shop on the Mile of the Magnificence (not the Mile of the Miracles). My advice to Manolo: get out in the ‘hoods! I love Michigan Avenue and Oak Street as much as any other shopping hound, but the plenitude of capitalism means that most of the shops there are ones you’ll find in other large cities: chains and department stores.
If you want to have fun with regional shopping when you travel in the US, I firmly believe that you have to seek out neighborhood shopping areas and boutiques. For a long time the boutique-y neighborhood street in Chicago was Armitage Avenue, which is still a shopping staple combined with great late-19th-century architecture. But over the past decade other neighborhood shopping has evolved, as more people look to shop in distinctive and non-chain shops.
Such shopping neighborhoods include my own Southport (with great shops like Freesia, Red Head, Trousseau, City Soles, Krista K, and Jake), Division Street in Bucktown/Ukranian Village (including a Zen yarn store called Nina), Milwaukee/North/Damen in Bucktown/Wicker Park (where my favorites are Helen Yi, Clothes Minded, and Jade), Wells Street in Old Town (with old reliables like Handle With Care as well as lots of new shops in the past year), and Lincoln Square (Traipse for shoes, Merz for European toiletries).
This Frommer’s entry on Chicago shopping is a bit out of date, but captures the essence of my argument.
Such places are where you get the real fiber of a place, so to speak. So Manolo, high thee to the neighborhoods to get super fantastic!