Shopping in Chicago
The Magnificent Mile has a lot of high-end stores (Tiffany, Neiman-Marcus, Macy's, Water-Tower etc.) and some regular stores as well (Crate & Barrel, H&M, etc). State Street has a lot of regular stores, if you are just window shopping I would head there first.
North of the Chicago River you will find two disrinct shopping enclaves: River North, home to gallereries and home-furnishing stores, and the Gold Coast, with its high-end boutiques.
The Mag-Mile has more than 450 shops, Art Galleries, Haute Couture, bargains and boutiques, it does not get any better for all of us that loves to shop. You can actually drop here!!