Midprice retail- LOOOOOVE Woodfield, I swear to God they have everything there.
Higher prices, but not ridiculous...gotta love downtown Highland Park, which has privately owned style shops (E Street Denim) that carry hard to find brands...Paper Denim and Cloth, Three Dot, etc.
I also love shopping at Old Orchard, since it's an outdoor mall with Nordstrom, Bloomingdales, and Steve Madden.
Still, if you're willing to pay for parking, shopping in boystown beats everything else, although most of the people that work there don't really like helping you if you're a girl from the 'burbs.