Upgrade Offers: the New “Holy Grail” of Travel Hacking?

Like many old-timers in this hobby, I used to rely on new signup bonuses for my travel hacking needs/wants. However, things have changed, and not for the better. To be clear, I’m definitely not in the “sky is falling” camp. Never was, never will be. I’m grateful for whatever I can get and don’t lose sleep over credit card denials.

And boy, there have been a lot of denials for me lately. I can’t even get a credit card from Bank of America! I could always count on it as the last-resort application, but not anymore. Don’t get me wrong, I still get approvals here and there, mostly from obscure banks. But I can say with absolute certainty that the good old days of travel hacking are over, at least for me.

But not to worry, there is more than one way to skin a cat. While I have been getting bonus qualification pop-ups for new Amex cards, I also got a few upgrade offers to make up for those fails. A few months ago, I had a chance to upgrade my Amex Blue Cash to Preferred version and get $250 bonus along the way.

It’s a great card due to 6% cashback bonus category on groceries. In fact, it has been on my “keeper” list from the beginning. I thought about applying for it anyway, and Amex upgrade offer made it a no-brainer. I didn’t get a new inquiry and didn’t get another account added to my credit report. Btw, I’m thinking about trying to get under 5/24 limit, so I can pick up some Chase cards. What’s happening to me?

Latest upgrade offer for Hilton Honors Aspire

My husband had Amex Hilton Ascend (aka Surpass) card that was coming up for renewal. I was planning to cancel it because I didn’t think I would be able to recoup the $95 annual fee.

It’s definitely a decent product for some due to Gold Hilton status and a unique Priority Pass access arrangement. Instead of unlimited airport lounge entry for up to three individuals, you get ten entires per year. Recently, I used five of them for my tribe.

So, this is a nice perk for large families who fly only a few times per year because it offers more flexibility. Of course, you can no longer use Priority Pass benefit tied to Amex cards for airport restaurants, so that’s a bummer.

Heads up! Through 8/28/2019 you can get 130k Hilton points+free weekend night on Amex Hilton Surpass after spending  $4,000 in 4 months (annual fee of $95 is not waived). The current signup bonus flavor IMO is the best it’s ever been. My personal referral link (I will get 20k Hilton points if you get approved).

Anyway, since I’ve recently converted my husband’s Chase Freedom Unlimited card to Chase Sapphire Reserve, I couldn’t justify spending another $95. Some airport lounges allow kids under 12 to enter for free, so my family of four would be covered in those cases. And you can still use Priority Pass from CSR towards airport restaurants.

So I figured as soon as the renewal fee hits, I would cancel Surpass. But then I saw an upgrade offer in his online profile. We would get 150k Hilton points after spending $4k in 3 months. We would also get all the perks that the new Aspire cardholders receive. Of course, we would also have to pay $450 fee upfront.

This isn’t an offer I would recommend to beginners, but like I said, I don’t have many options these days. Beggars can’t be choosers. Of course, I’m not just going to pay $450 fee without running some numbers first. After all, we are in this hobby for “free” travel, aren’t we?

Let me show you my thought process, and hopefully it will help you with your own Amex Aspire upgrade offer dilemma.

Free weekend night

I wasn’t sure if upgrade offer would still give me a free weekend night. After a Google search it appears that the answer is Yes. Mark at Milestomemories blog got it on his and his wife’s Ascend to Aspire upgrades. I live in central Florida, so there are a lot of nearby options for a fancy weekend getaway. However, I like spending more than one night when driving somewhere for two hours.

Instead, I think I will utilize it at Homewood Suites San Diego Downtown/Bayside hotel (60k points per night). We will have to spend one night in San Diego on the way to Hawaii, so this hotel will be a perfect fit. Sure, I could use my “free” night at Hotel Del Coronado  that goes for 95k points.

However, the latter is further from the airport, and rooms have two queen beds. Homewood Suites property has, well, suites with two queen beds and a sleeper sofa. Since we are traveling with kids, having more beds is welcome news indeed.

Value to me: $150

$250 airline incidentals credit (based on calendar year)

I’ve never really bought airline gift cards in order to utilize this perk, so recent negative changes had little impact on my decision to upgrade. I know there are other ways to maximize this credit, like paying taxes on Southwest award tickets and then canceling them afterwards. Be aware, Amex may claw back your credits later on, so be careful.

Besides, it’s not something I plan on doing anyway. I did pay Jet Blue award ticket taxes with my now-cancelled Amex Gold and they were reimbursed. But it was a legitimate expense, and I wasn’t counting on credit. I’m not going to complain if I receive it, but I won’t go out of my way to get it in a roundabout manner. At least that’s my policy, but everyone should do what they are comfortable with. I ain’t judging.

Anyway, there may be a way for me to utilize this credit in a legitimate manner. You see, I’ve booked award tickets on American from Tokyo to LAX. My elderly in-laws are supposed to come with us, so I’m thinking about paying to upgrade them to Main Cabin Extra (more legroom) for $120 each.

It should code as a seat selection, at least according to recent data points. My sister-in-law planned to pay cash for it anyway, so why not get a reimbursement while we are at it? The credit is based on calendar year, so if this works, I might get me and my husband (who is very tall) upgraded in January of 2020.

Value: $480 if everything works as intended, $0 if it doesn’t.

$250 Hilton resort credit

This is a niche, but very lucrative benefit. If the stars align, it can be almost as good as cash. As it turns out, I’ve already booked two nights at Baker’s Cay Resort Key Largo. I wrote about it awhile back and mentioned the ability to reserve a junior suite for regular rate of 60k points per night.

To be fair, junior suites there are very small, but it’s OK. What matters is that bedroom area is separate from living room, something that is very important when we travel with kids. It gives me and my husband some privacy and peace.

I wasn’t planning on  eating dinners at the hotel, but now we definitely will. I figured between margarita drinks and an evening cruise (all charged to the room, of course), it won’t take long to spend $250 credit organically without even trying.

This looks like my kind of place!

Value: $200 (I would buy a Hilton gift card at a 20% discount since we plan on going to the resort anyway)

Diamond status

It’s hard to determine true value here because my husband would have Gold status if it wasn’t for this upgrade offer. So, we would get the free continental breakfast for two, plus a possible room upgrade. Due to having Diamond status, we may get a suite upgrade, but I’m not holding my breath. We should earn extra Hilton points on dining, but it’s unlikely to add up to a big amount. See my post on which status I would chase if I were a road warrior

Value: TBD

Airport lounge access

We already have lounge access via CSR, so the value here is $0. It’s a free ride, but you’ve already paid (hat tip Alanis Morisette). I probably would still upgrade Freedom to CSR instead of Sapphire Preferred even if I knew that this offer would be coming our way. I just used $100 Global Entry credit for my mother-in-law, and am in the process of burning my UR stash on travel at 1.5 cents per point.

I’m a little annoyed that my husband got the upgrade offer and not me. That way lounge access would come in handy for times when kids 12 and over have to pay to gain access. Unfortunately, you can’t use two Priority Pass cards for the same lounge entry. Yes, I’ve checked.

Value: $0

Grand total: $350 conservative value in worst-case-scenario

As you can see, even if I don’t maximize all the perks, I should mostly recoup the annual fee during the first year. In best case scenario, I will come out way ahead.


What about 150k points?

This is, obviously, the biggest reason I accepted the upgrade offer. All those other perks are sweet, but not sweet enough to cough up $450 upfront, especially when factoring in the uncertainty of travel with young kids/decrepit in-laws. The good news is, Hilton chain has a huge footprint, so possibilities are endless. And unlike certificates, Hilton points don’t expire as long as you have some activity every 12 months (earning or burning).

I’m tentatively thinking about using the bonus towards a 5-night stay at DoubleTree Suites by Hilton Orlando-Disney Springs Area The cost is currently 50k points per night, and you get 5th night free as long as you have some sort of status with Hilton. My husband has a regular no-fee Hilton card (Silver status) which we plan to keep open.

Our general strategy for Disney is avoidance. I don’t hate Disney, but I don’t love it either. Despite living in Florida, we rarely take our kids to see Mickey and the gang. But as the saying goes: the time has come, the walrus said.

Recently, my son found out about new Star Wars Land opening in Hollywood Studios. So, over the last few days he has been calling my husband and saying:”Hello! This is Disney World. We’ve heard you have a young son. Would you like to purchase tickets to Star Wars Land?” Ugh, evil Disney machine strikes again! Dumm dumm dumm.

It will probably be a year or two until I feel our budget can handle it, but a visit to Disney parks is looking very likely. I plan to time it with Florida Resident Pass that offers four days for around $200 per person. That’s where Hilton points will come in handy. Nancy has written a post on Disney Springs hotels that offer on-site benefits like 60-day FastPass and Early Magic hours.

The 60-day FastPass to me is the most valuable perk of all, and would justify the relatively high points cost of  hotels on the list. Right now the benefit is valid through the end of 2020, but I’m hoping they will extend it.

The reason that DoubleTree Suites by Hilton Orlando-Disney Springs Area caught my eye has to do with having a separate bedroom area for parents. I don’t know about you, but the idea of spending five nights in one room with the kids makes my eye twitch. There is a pool and a hot tub on premises, and that’s all we need to make our kids happy during evenings.

Bottom line

The main purpose of the post is to encourage you to analyze your personal situation before jumping on any offer with $450 annual fee. You want to be reasonably sure that you can come out ahead via your existing travel plans.

Free travel in this hobby can get very expensive, fast, especially when you start adding extra trips. Life is unpredictable, so it’s important to have  Plan B for your points or certificates. Related post: I’m happy to pay annual fees on these cards (and one I would never renew)

In my case, taking advantage of upgrade offer on Surpass card was pretty much a no-brainer. As I’ve said before, most banks these days don’t want me, and the ones that do usually don’t have compelling offers anyway.

Are you tempted to upgrade to Aspire?

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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8 thoughts on “Upgrade Offers: the New “Holy Grail” of Travel Hacking?

  1. Pingback: Should You Risk Buying Third-party Gift Cards with Amex Products? - Miles For Family

  2. Pingback: New Travel Hacking Holy Grail, Modern 7 Wonders of the World, 25 Lighthouses Worth Checking Out - Miles to Memories

  3. I like your analysis. I did the same thing earlier this year and decided to go for the upgrade offer. I was able to snag $200 in gift cards with WN before that option disappeared. I was hoping to get $200 more in January but that won’t be happening as easily now. I used the free night for a $300 beachfront hotel night. That plus the $200 gift card, 150k points, and diamond status is easily worth it. I will likely change my airline back to AA in January and buy food/drink for my seat neighbors with my $250 credit. I already had some other premium cards that get PP lounge access so that didn’t factor in to the equation.

    • @HawaiiDreaming Thanks for stopping by! I like your name, it describes how I feel right about now.
      It sounds like upgrading to Aspire was the way to go in your case as well. The annual fee is a bummer, but it’s not too hard to get enough value to cancel it out. You may want to use up your $250 credit on seat upgrades, though treating your seat neighbors is a pretty cool way to do it, too.

      • Thanks Leana. I am a big fan of the islands. I can’t get back soon enough.

        After doing some research, there might be a way to still get some WN credits by buying cheap flights or using some gift cards with a more expensive flight. My seat neighbors may not get free food/drink after all. 🙂

      • I’m sure your seat neighbors will be just fine! 🙂 I love Hawaii, too. It’s been so long since I’ve been there, but I’m hoping we can stop in Oahu next year on our way to Japan.

  4. I used Penfed Amex to buy “economy extra” for $118 on 7/25. The transaction description is “AMERICAN AIRLINES 4510739800-433-7300 TX” yet so far the expected $100 reimbursement did not post.

    • @af Interesting. I wonder if Penfed card codes it differently from cards issued directly through Amex. It’s totally possible I won’t get reimbursed, and I’m not really counting on it.

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