Downtown, Michigan Ave. has a lot of high end stores if you’re willing to shell out moola. There’s a lot of cute boutiques if you drive down Evanston. The malls… Woodfield in Schaumburg, Old Orchard in Skokie, Gurnee Mills which is an outlet mall, and Hawthorne Center in Vernon Hills (which has good, low taxes.) Those are my personal favorites.
Personally, I don’t thrift so I’m not sure about where those places are. :|