I've considered doing the bill pay thing from my Wells Fargo account; essentially sourcing the transfer from WF instead of Chase, right?

I'm not sure how comfortable I feel doing that with 8k+ though.

I've never really understood why you aren't able to put additional funds on your account extending it above your credit limit. I know this isn't done in the US but I would do it regularly in Canada with all cards I've owned (Amex, TD Visa, RBC Visa, etc). For some reason it's not possible to do this in the US. It would sure simplify things as I could pay the sum of the pending transactions right now even before they're reflected in my balance. As it stands, Chase only allows you to make payments in the maximum amount of the balance due.

Strangely, none of the pending transactions are from restaurants or anything that might be subject to change either. They are mostly for travel costs through an agency (hotels, tours, etc) and store purchases (clothing). Two of them have been pending since Saturday afternoon.