My Chase Ultimate FRUSTRATION reward(s) – I miss the way booking used to be so much!

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chase UR logo

I have loved Chase Ultimate Rewards (UR) points for a long time. Even before the Chase Sapphire Reserve card came out I found great value out of the plain old Chase Sapphire card. I have had two amazing visits to Grand Cayman each paid for by burning large chunks of UR points and even added the diving in with the package.

connexions loyalty now powers chase UR points spend

But it has been a while since I redeemed for such a vacation and things have really changed for the worse. Apparently I missed it that a little over a year ago Chase enlisted Connexions Loyalty to run the reward redemption. When it works, great, but when it does not work you run into the frustration and endless loop I fell into.

stt failed booking

You see in the past, if I wanted to dive as part of my stay, the dive outfit would bill the hotel and then make one big invoice. Next, the UR folks would simply call the hotel and pay the bill in full in advance with my points. Quick, simple and great value. Now, not so much and when things go wrong you are in trouble because now, since they go Chase>Thrid Party Vendor>Hotel you are stuck when IT goes sideways.

stt pending

In my case I was simply trying to book what was shown on the Chase web site with points plus a few dollars. Should be simple right? I tried for DAYS. UR reps tried for DAYS. At the final check-out page I got what drives us Delta flyers crazy when the similar situation happens – this rate has just sold out. Great. But then when you go back it is “magically” back again at the exact same price. That is until you go to check out and then – ERROR – it is sold out again. But you see it wasn’t really.

stt room2

I called the resort I am going to stay at and guess what, the space was WIDE OPEN for this price and the hotel rep was not pleased that we could not get this stay booked.

Enter the rabbit hole of IT frustration.

Chase rep after Chase rep (well really Connexions rep I guess) could not get this done. They could not call the hotel direct to book, but they tried and failed because it HAD to go via the 3rd party booking software or no joy even though the Chase site showed availability and the hotel showed availability at this price.

In the meantime the very low Delta priced flights I wanted to book, but did not until I could confirm the rooms, went up day by day by day. Thanks Chase – you cost me on this one!

In the end I did get the trip booked. I had to change the dates around a bit to not pay hundreds more in airfare and Chase did give me a few thousand points for taking the better part of a week and hours and hours on the phone to get what should have been simple to complete.

Bottom line is technology can help or hurt us. Delta, with their horrid SNAPP program, blocks so much that a competent rep once could do. Now that Chase has removed so much power from their reps I value Ultimate Rewards a lot less than I once did. Sure they will still be in my travel mix but I find it amazing that cash back cards are becoming more of a draw to me than ever before. Maybe it is becoming the same for you as well. – René


  1. I booked multicity flights for 2 from HKG to various cities in the USA returning to HKG in 2 weeks recently through Chase. When researching flights and costs that would fit the plans I found that the fares changed each time I attempted to search. (even in the same login session) As I attempted this over a few days there was a range of $400 for each ticket.

    I finally chose the lower fares that appeared on the 4th day of attempts before the flights went through the roof.

    This was so much like booking Delta flights that it makes me seriously wonder if my ISP number is recorded and the price goes up each time I check.

    These “free” points sure do have a significant cost in time and extra charges when we attempt to redeem them.

  2. I hate to say it but I’m sure this is part of the credit card companies scam. They’ve lured us in and can change the deal anytime they want. And same goes with the airlines.

  3. Thanks for the heads up. I too remember the old days, when Chase Manhattan and First USA first got together to create this angry mongrel of a credit card company. Back then it was a great program. Booking award flights was a breeze. One time, my mother needed a last minute ticket to Hawaii to get to a wedding. After I spent hours on Travelocity trying to find her the best tix, one call to Chase and they found her a ticket that Travelocity didn’t even show.

    No longer. That “points are worth 1.5x if used for travel” Chase marketing is BS. It’s time to admit that Chase has no value unless we are gong to transfer the points out to a partner.

  4. I have had so many issues with their website. It is easy to earn the ultimate rewards but nearly impossible to redeem them through their travel portal. I think there will be a lawsuit as they advertise their CSR points as worth “1.5 cents per travel” when you cannot actually use them that way.

  5. @David – A lawsuit would not shock me one bit. Chase needs to clean up their act and stop with the #BaitAndSwitch they have going on. In the old days the product worked – now, well…. 🙁

  6. Hmm… i book delta tickets and rental cars all the time from UR. The rental cars are usually quite a bit less than discounted searches on And the Delta flights have always been the same price as Delta’s site. Easy to book no problems here.

    The only prob i’ve had is cancelling Thrifty cars. U need to call in to do it.

    UR Still my 1st choice.

    Maybe it’s just keeping it simple with redemptions?

  7. I’ve booked on UR plenty of times and never had an issue. I find the interface slick and simple. I’m sure the issue you had was a supplier issue and not necesarrilly a Chase issue. You see, the suppliers feed the stock of hotels/flight/etc. on the site. If the supplier says there are no rooms, then the site will error once you try and book. Good luck and hope things get better for you.

  8. I’ve been having the same problem – thank you for this post, I was looking for a sanity check. 4 out of the last 5 flights had this issue, I’m surprised I ever got anything booked at all. One of the flights the rep was able to remedy the situation by filling out the form manually instead of through the software. It’s really an awful headache and such a shame when I feel like I can’t use my points.

  9. I’m running into this problem as we speak, first time I’ve ever seen it happen. Google Flights is showing me an available flight with 7+ seats on each connection. I go to UR to book it and “this itinerary just sold out”. I go to American Airlines site, and this particular itinerary has loads of seats available. What? This is seriously a hassle to me.

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