For ready-to-wear, Morris & Sons is certainly worth a visit for discounted quality men's clothing (Brioni, Luciano Barbera). Although some have reported less than satisfying visits to either the Chicago or New York location of Paul Stuart, I think it's still worth a visit. The Chicago location is a beautiful men's store, albeit apparently smaller than the NY location. During my last visit to Chicago, the shoe salesman I talked to was friendly and familiar with English shoemakers. I inquired about the availability of Edward Green in Chicago. He checked in with his manager and came back with George Greene, a men's store on Oak St, and Polo Ralph Lauren on Michigan Ave.
Chicago store recommendations (AskAndy)
Dining and entertainment recommendations (AskAndy)
A 1964 Time magazine article on Chicago-based RTW manufacturer Hart, Schaffner & Marx