B.J.
Hi K.:
The best place to shop for you and your child in one sitting is MARSHALL's (inner ring suburbs such as Oak Lawn-95th & Cicero or up north-Belmont and Clark and downtown Chicago). They have brand names for both kids and parents, designer fashions and handbags at reasonable prices.
Another place for "you" and your child's clothes is JC PENNEY. They have cute clothes for career women under the brand name WORTHINGTON and they have sales all the time (coupons every week) and the clothes last forever.
I have also had great luck at THE CHILDREN'S PLACE and OLD NAVY for my 6 year old son.