I used to live near Chester and really miss it. It's a lovely place to wander around and good for shopping. A lot of the shops are under cover (The Rows) so even if it rains you won't get too wet.
If you're staying outside of Chester then consider using one of the park and ride services rather than trying to park in the city centre. On Saturdays the place is packed!

Cheshire Oaks outlets are also quite close by.

We have picked Chester for our 'sisters weekend away' this year. There are 5 of us and we try to get around the country and sample the delights of different areas.
I have been to Chester once before on our way to Wales but just had time to stroll around-took in the black and white shops (cant remember what the area is called)and saw the Roman amphitheatre.Thats about all I can recall.
This time we will be there for 2 nights and can travel around a bit more. I think we are doing a ghost walk but thats about as much as we have planned so far.
Anything must see or do. Any good places to eat -not too pricey ,we are all on budgets . Any hidden shops /outlets in the area.
Things to do on a cold wet day maybe.

Looking forward to exploring this area.