Consider Independence on Oak Street for shoes from Oak Street Bootmakers. They are great for casual shoes. One street south on Delaware is the Church's store, which is the Chicago outpost of the famous English shoemaker. You also have all the high-end department stores like Bloomingdale's, Barney's etc. within a few streets of each other.
For deals, consider Nordstrom Rack near the same area. You can also try the new outlet mall in Rosemont, very nice the ORD airport.