If you are staying at Chatham Hills, then there are lot of places to go out for shopping. Most of the time you can go by bus. (SMTD - It would take time for you to understand the System Map as I still don't understand it completely)
The next thing you would visit more often is White Oaks Mall (And all the shops around it) - Half an hour walk.
These are all the stores in and around White Oaks Mall. (The best of all in Springfield)
There are lot more that the map doesn't show in here but you can see it on their website directly in here
Click Here
Next place where you would often go is Walmart - This is again a half an hour walk.
The most visited spot according to me is
Shop'n'Save - 15 Min walk
The next thing you would visit more often is White Oaks Mall (And all the shops around it) - Half an hour walk.
These are all the stores in and around White Oaks Mall. (The best of all in Springfield)
There are lot more that the map doesn't show in here but you can see it on their website directly in here
Click Here
Next place where you would often go is Walmart - This is again a half an hour walk.