Chase Sapphire Preferred - Pay Yourself Back - Gas Stations/Grocery Stores

So... I'm not well versed in any of this. I haven't tried to manipulate/move the points around beyond moving from my Freedom to the Sapphire for travel. I did find the booking through Chase to be well worth it and cause zero issues. I checked the deal sites for flights and hotels, and then when I checked Chase, the prices were the same (although some hotels were not available). I booked through Chase for international flights and hotels and saved $150 just on the one trip. Considering the card has travel insurance built in it seems like a non-issue.

Yes but I wouldn't advise it. Their customer service isn't great. It'll work fine until you need help with something and then you'll spend more time than it's worth. A lot of folks report back that the pricing isn't competitive, plus they book a tier of fare that is ultimately some kind of "bulk" fare, meaning if you have anyone other than Chase look it up, it will seem like you paid much less. Usually not an issue unless you are owed a refund or credit or need to make a change. Some carriers even charge a fee to 'take over' the reservation that they book, before making any changes.

Again, this is never an issue when everything goes smoothly, and your booked travel takes place with no hiccups. Sometimes even the changes go smoothly. But for those that have used them extensively and experienced the problems..... never again. I wasted so much time that I eventually just punted the 40k+ pts I was owed. The money just wasn't worth the hours I was wasting.

The card and rewards are great but I do not advise anyone to book through their portal. Transfer to travel partners.

You're right as a general rule though; portals/3rd parties in the mix only complicates issues and often times makes what would be simple resolutions very complicated. For example, booking through a 3rd party (expedia et al) makes it such that even hotel reservations cannot be cancelled or modified at the desk/by the hotel. Plus, direct hotel reservations receive priority if there's a bumping situation. You might be saving $$ but you're opening yourself up to the possibility of huge issues.

All anecdotal. I'm on several online groups and the stories are staggering. The number 1 rule in ALL of these groups to any newcomer is simple. Do.Not.Use.The.Portal.

Travel insurance will not even remotely help the issue that I'm describing. For example, you need to reschedule a flight but the airline won't handle your booking without charging a fee. Chase customer support will put you on hold for hours and then tell you to call the airline. Rinse and repeat. Or, you are owed a refund after you booked with points. The airline processed it. Chase doesn't post them. You call and they tell you it takes 1-2 billing cycles. You call back and they say it could take another billing cycle. (PS- each of these calls involve hours of hold time). Again, rinse and repeat.

Personally, my experience was on a flight booked with a Delta credit during COVID. Delta downgraded my ticket and owed me a credit. After many hours dealing with Delta (not related to using the CSR), they finally refunded me what they were supposed to, but not as Delta credit. They refunded it to where my original flight was booked, which was via Chase UR points. They never arrived. Each call is an hour of wait time minimum, plus more as they escalate the issue. They almost all resulted in saying they would call me back (never happened once) or that the resolution would take 1-2 billing cycles (never resolved). I did spend SOME time trying to recover 40k pts, as that's supposed to be minimum $600 in value, but eventually I had spent enough hours wasted on this that it just wasn't worth my time. My particular circumstances may be unique, but in talking to many people, the "we'll call you back" and "it takes 1-2 billing cycles" is an extremely common occurrence to get you off their back. Nothing happens.

I'm always one to say take everything with a grain of salt. Believe me or don't believe me. But one universal thing that I always hear from the folks who have these experiences is that the portal works perfectly fine.... until it doesn't. And when it doesn't, it's a doozy. It doesn't hurt ME if you use the portal, I have no reason to relay this to you other than as advice from someone that may have more experience. I once had your attitude. I'm doing everything by the book and I know how to do this so the portal works fine. It was hubris. The travel portal used to be run by another company (rumored to be Expedia). Chase took it over entirely a couple of years ago. It is hot garbage unless nothing goes wrong. Again, nothing will go wrong MOST of the time, but don't get lulled into thinking this is somehow a good record for Chase. When nothing goes wrong, the customer service didn't do anything right, they merely had nothing to do. When you NEED them to do something, they fail at a startling high rate. Don't take this risk.