Hi there having done this trip loads while our boat was moored at Anderton....my advice would be to push on for Chester. If you get to the boat yard handy around dinnertime hopefully your boat will be ready & you'll hopefully be able to set off by 2pm. Its a nice leisurely 4hour cruise to Middlewich but I'd aim to do an extra hour & go up the locks & moor above Wardle lock on the Middlewich branch or carry on a little if you want a rural mooring. Sunday I'd aim for a nice early start with 3 hours cruise to Barbridge Junc although this can alter massively depending on if there are queues at the locks. From Barbridge junction to Beeston wharf is around 3hours again depending on Queues at the locks. But the joy of this stretch is that 2 boats can share the locks apart from beeston Iron lock.
From Beeston to Chriselton is around 2 hours cruising so I'd plan to moor around here Sunday night.
The Monday morning you just have to head down the 5 locks into Chester city centre. This should take around 2.5 hours again depending on queues. I'd moor on the visitor moorings by the lock keepers pub think its bridge123c as this is quite near to train station. Hope this helps you.