Why I Converted Chase Freedom to CSR, and Why Ultimate Rewards Travel Portal Is a Mess

  1. A Leap of Faith: Booking Seven Award Tickets to Japan/Hawaii

  2. Tips and Tricks for Booking Awards via Avianca and Asia Miles, and why I’ve Fallen  in Love with Amex Membership Rewards

  3. Why I Converted Chase Freedom to CSR, and Why Ultimate Rewards Travel Portal Is a Mess (this post)

  4. Choosing the Best Mileage Option to Hawaii: the Good, the Bad and the AAdvantage

A nice thing about Ultimate Rewards points is that you can collect them via cards like Chase Freedom or Chase Freedom Unlimited and pay no annual fee in the process. Of course, you won’t be able to transfer them to travel partners like Hyatt or United, nor get an uplift on travel redemptions.

But it allows you to avoid paying an annual fee until you find the right opportunity to put your points to excellent use. For me that opportunity was now. Over the last few years I’ve amassed 63k non-transferrable Ultimate Rewards points by maximizing 5% categories on my Chase Freedom and using Chase Freedom Unlimited for unbonused spend.

Occasionally, I do something really dumb. Just the other day I was planning to buy an Amazon gift card at the gas station with my Chase Freedom  in order to earn 5 points per dollar. I got distracted and accidentally used my Discover card which will get me a whopping 1% cash back.

Photo by FuYong Hua on Unsplash

I know how you feel, kitty.

Anyway, since I’m currently planning a family trip to Japan and Hawaii, I was hoping to find a sweet spot for my stash. As mentioned earlier, I was able to cover airline award tickets via Amex Membership Rewards and various mileage currencies. So, I figured I should try to use my UR points towards hotels.

Sadly, the places I liked were not available via Chase travel portal. But I could book them via AirBnB (my referral link, you will get $40 towards a rental and I will get $20) and Homeaway.com, which is what I did. As much as I like using points, they aren’t always the right fit.

Btw, if you are heading to Kyoto, there is now a unique Hyatt property where you can use your renewal certificate from Chase Hyatt credit card (my personal referral link). All rooms seem to have double occupancy, so not really an option for us.


Besides, I really wanted to stay in a traditional machiya house,  something you can only do in Japan (watch this YouTube video to learn more about machiya). The place I booked is at least 110 years old, yet has all the modern conveniences. I don’t feel comfortable sharing the AirBnB listing at this time since I’m not sure how the owner would feel about it.

The cost was $250 per night (2bedroom/2bath), so not bad at all. I recommend you always look beyond chain properties when traveling overseas. And yes, you can definitely book machiya homes via Chase travel portal as well, just not the one I wanted.

One thing I wasn’t sure about was our two-night stay in Tokyo. I really wanted something central that doesn’t cost an arm and a leg. I also didn’t want to share a rental with my in-laws n order to avoid potential conflicts. A tall order, indeed. The best deal in the city, by far, is Hyatt Regency Tokyo that is a Category 3 (12,000 points per night). That makes it eligible for renewal Hyatt certificates via co-branded Chase Hyatt card.

Unfortunately, the room will only fit two people. I’ve emailed the hotel and they said they can upgrade the certificate to room that fits three, but that will cost an extra $90 per night, including a rollaway. That would take care of my in-laws, but what about my family of four?

And then I’ve discovered this sweetest of all Hyatt suite deals, pun intended. Behold the Atrium suite:

That’s $2,500 per night and includes lounge access. Yet it costs only 20k Hyatt points, though you have to call in order to book it. That’s when I hit a snag: occupancy limit is two people, despite the fact that it has a large couch and two queen-size beds.

I emailed the hotel and they said they will make an exception since our kids will be 9 and 12 at the time of the trip. They even offered to put a rollaway in the living room at no cost. Yes, please. Obviously, $2,500 per night is insane and not something I would ever pay. But 20,000 UR points, food included? Now we are talking.

Unfortunately, it looks like the hotel is blocking the dates around the Olympic Games dates, though you may be able to book an award room over the phone. Won’t hurt to try, that’s for sure.

Now I just needed to convert my husband’s Freedom Unlimited to Chase Sapphire Reserve ($450 fee). We wouldn’t get the sign-up bonus, but neither one of us are eligible anyway due to 5/24 rule. CSR comes with a lot of perks on top of ability to transfer to travel partners. I figured we may put lounge access to good use, specifically in participating airport restaurants where you get $ allowance. Amex is discontinuing this option. Plus, the ability to get 1.5 cents towards travel is nothing to sneeze at.

On top of it, the card comes with $300 travel credit which I was able to utilize right away. The card also has excellent travel insurance coverage, so I used it to pay award taxes on my in-laws’ tickets. Sure, they bought a standalone policy as well, but it won’t hurt to have double coverage, just in case.

We had to call in because Chase rep refused to convert the card via secure message. Amazingly, the points became transferrable immediately after the phone call. So, as long as you have points in your Freedom/Freedom Unlimited accounts, you may gain access to travel partners within minutes, in case a need for frequent flyer miles arises suddenly. Like me, you can just wait for an opportune time.

I was able to transfer 40k UR points to my husband’s Hyatt account and two nights in the suite were booked via a phone call to Hyatt. Done and done.

Utilizing the rest of the stash

Like I said earlier, I decided to book vacation rentals via other websites. Well, all except our stay on Miyajima island. But it looks like I’ll have to go through Rakuten Travel for that because Chase portal doesn’t list the onsen hotel that I like. One place where I could utilize my Ultimate Rewards was car rental in Hawaii.

Sure, the trip is a long way off, but I figured might as well burn the stash now and get 1.5 cents per point. Huh! That proved to be easier said than done. I’ve tried to book the car rental online for two days, to no avail. I even called and was told that it happens sometimes, and to try again later. If you know that it happens, then fix it, for goodness sake! People are paying $450 fee for this card.

I’ve even reached out to Chase via Twitter, and a rep suggested to call. The problem is, the card is in my husband’s name, so I had to get him on the line to give permission. Fine, let’s get this car booked. Unfortunately, Chase rep has encountered the same error. He told me to try again later. I insisted on talking to a supervisor, but instead, after a long hold he connected me to an overseas department.

First, the lady didn’t speak very good English. She was super nice, we just couldn’t understand each other very well. I kept asking for a quote on SUV, and she would tell me a price on a Hyundai Elantra. Fine, let’s book it, I don’t care. I also checked Kayak.com and the price she was quoting me was $20 more. So, not really 1.5 cents per point, but OK. I should add that the prices she quoted me did not match what I was pulling on Chase Travel portal. Insane. No wonder the car rental booking wouldn’t go through online.

A silver lining: during the ridiculously long holds I remembered that most car rental companies add a fee for an extra driver. I did a quick online search and saw that  Enterprise doesn’t add a fee for spouses, so that’s the one I picked. After two hours the car rental was finally booked. Pop the champagne!

The reservation has a free cancellation until three days before the rental, but I’m not sure I want to mess with it. I was curious if others have experienced something similar recently. That’s how I came across this post on Seat31B: Chase’s terrible, horrible, no good, very bad travel portal.

Well, the title says it all. Sure, it’s possible that mine and author’s experiences are a fluke. Anything is possible. In no way am I suggesting that everyone deals with this type of nonsense when redeeming UR points via travel portal. I know that my cousin-in-law has been very happy with this  feature of the program. It’s just aggravating to go through so much trouble to book a simple car rental.

Still, overall, converting Freedom to CSR was the right decision at this particular time. If using up the rest of my points on revenue travel proves to be too much of a nuisance, I can always dump my stash to Southwest program. And of course, after one year is up, I’ll downgrade my CSR again until another outsized-value redemption opportunity presents itself. Maybe in three or four years the portal will be fixed. Wouldn’t that be nice?

Note to new readers: Chase Sapphire Reserve is one of the products I recommend as your two-year beginner strategy. The card pays us commission if you feel inclined to support he blog. 

Click here to view various credit cards and available sign-up bonuses


Author: Leana

Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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11 thoughts on “Why I Converted Chase Freedom to CSR, and Why Ultimate Rewards Travel Portal Is a Mess

    • @Nancy Thanks! It was a great find, for sure. Not exactly dirt cheap, but a good value in my book. Since there is a decent chance of my in-laws canceling their portion of the trip due to health reasons, it’s nice to have lodging that doesn’t depend on their plans.

  1. Don’t forget to register for the priority pass – I almost did not get mine before my trip because I didn’t realize I needed to do that!
    Southwest note – I didn’t think you could convert UR pts to Southwest RR pts – only buy tickets for Southwest. Or am I mistaken?
    Thank you for posting this tip. I struggle with paying the annual fee but love the freedom of UR pts + ability to combine UR pts from Freedom cards. I worry that they might say no to the upgrade if I do this. How many times have you done this so far?
    Thank you for all your wonderful helpful stories!!

    • @Clyn6 Good point on registering for Priority Pass! I haven’t done it yet. I did have CSR in the past and now remember that requirement.
      On Southwest: Chase UR points definitely transfer to Rapid Rewards on 1:1 basis. In fact, it’s the only program that partners with Southwest. As far as upgrading/downgrading Freedom Card, it’s not something I recommend doing on a regular basis.That’s why I waited for the right time to do it. We’ve never upgraded my husband’s Freedom Card before, so I doubt Chase will take an issue with it. Besides, we are paying the annual fee. As far as downgrading back to Freedom, again, I don’t think it will be a problem. They can’t make us pay a fee we don’t want to pay. And if there is a an issue with the downgrade, I will simply cancel it. I still have my Freedom Card, and we rarely maximize the 5% categories on it as is.

      • Thank you for that helpful tip!! I did not know I could transfer UR pts to SW RR pts, that is a fantastic deal!

  2. I also had a really hard time using the Chase portal to book a rental car in Hawaii-I had to call in, and the rep told me to try again later. It did work eventually, for no rhyme or reason that I could tell. When we were in Hawaii, the rental car agent said that there was no charge for additional drivers in Hawaii (this was a Dollar and a later Budget rental, but the agent said it was a Hawaiian thing).

    • @Andrea That’s interesting that the rep said in Hawaii the spouse can be added for free. I Googled it and couldn’t find anything in writing confirming this policy, but maybe it’s a new thing. Regardless, Enterprise doesn’t charge extra, so we should be good. I’ll keep watching the rates on car rentals, and will rebook if needed, though won’t cancel the other reservation until new one is confirmed! I hope Chase will fix its buggy travel portal.

  3. I can’t wait to read about this epic trip. The suite sounds awesome! Japan is maybe my number one want-to-go-to destination right now. Just have to wait until my kids are a little older.

    • @Lindy Thanks! At this point I just hope the epic trip materializes. Lots of unknowns, including my in-laws’ health. But I guess that’s the case with most people of my age who happen to have elderly parents.
      Yeah, we had to wait till the kids were a bit older before I would even consider it. I know people do this type of trips with toddlers, some even drag car seats. No way, Jose!

  4. Pingback: Upgrade Offers: the New "Holy Grail" of Travel Hacking? - Miles For Family

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