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Dumping Chicago for Netherlands (Sort of)

Some of you might remember my post on using Spirit miles and Wyndham points for a short anniversary trip to Chicago. The idea was to get away as a couple while my in-laws took the kids on a separate trip. Everything was set but as fate would have it, for various boring reasons they had to schedule their getaway on a different weekend.

Of course, our Spirit flights were already booked, and unlike Southwest, you can’t re-deposit the miles for free. The award cancellation fee is so high, it actually makes sense to just let the miles go, especially since I booked at off-peak price (5,000 miles roundtrip). My in-laws were very gracious and said they could just keep the kids both weekends.

At first, I got  excited because I would get a double break from the madness. But the more my husband and I thought about it,  the more we didn’t want to be away from our children for 6 days in one month. So, I decided to rebook everything. Unfortunately, the new date didn’t qualify for off-peak Spirit pricing. In fact, even flights that cost 10,000 miles one-way were gone at that point. But I have plenty of Rapid Rewards points, and Southwest flies non-stop from Tampa to Chicago. Perfect!

Unfortunately, when I looked at the flights on our dates, they were running at 18,000 Rapid Rewards points roundtrip. It’s funny, paying 5,000 Spirit miles  was not an issue, but this new price gave me pause. After all, I could redeem 18,000 Southwest points for $180 Walmart gift card.

Another problem was maximizing our time in Chicago. You see, originally, my in-laws were planning to take the kids for only two nights. But then it turned into four. So, I started thinking, we might as well fly to Chicago and spend more than two days there.  The problem is, I only had enough Wyndham points for two nights, so would have to book a third one via “Go fast” rate. It would set me back 3,000 points+$150 (plus tax).

Free or not free, that is the question…

I could also convert my Chase Freedom to Chase Sapphire Preferred and dump my 37,500 UR points to Hyatt. That way, we could book Cash+Points rate at Park Hyatt Chicago and get a nice suite plus free breakfast due to my husband’s Diamond status.

It would cost me 12,500 Hyatt points+$150 per night. Let me think about it…  No way, Jose! Those 12,500 UR points could be redeemed for at least $125, and I have to pay  another $150 (plus tax) per night on top of it? Oh yes, but free breakfast and suite upgrade. How are they free now?

Chicago started losing its appeal, plus, my husband felt kind of “meh” about it to begin with. I was happy to go when it was going to cost me 5,000 Spirit miles and no extra cash copay for Wyndham Grand hotel. But now, faced with decision on whether to shell out a ton of Rapid Rewards or not, I was leaning towards the latter.

In fact, my cheap nature started telling me that maybe we should just stay home and have a local getaway using IHG points. We can sure use extra cash in our savings account. Amazingly, it was my husband who convinced me that we should just fly somewhere. How often do we get four days all to ourselves? And he was right.

Chicago, Saba or Aruba?

My dream for the last fifteen years has been to go to Saba. I’m fascinated by that island, but it sure is hard to get to (two connections from Orlando), which is probably why it hasn’t yet turned into a tacky tourist trap. Sigh… Maybe another time. Convenience and accessibility wins when I’m traveling with my husband.

I started looking at Chicago again as well as several other destinations. I was intrigued by possibility of going to Aruba, the Dutch Caribbean territory. Southwest flies there from Orlando non-stop, so we wouldn’t have to deal with connections (a deal breaker for my husband). I found flights for 19,000 Rapid Rewards roundtrip, plus $70 in taxes per person.

Aruba also has a Holiday Inn Resort that runs at 30,000 IHG points per night. As a holder of IHG co-branded card, I would get 10% of my points back. Not bad. Even though October is low-season in Aruba, flexible rate is still $165 per night (plus tax). Also, the island lies outside of hurricane belt, so we don’t have to worry about being stuck and unable to get back to our kids. I went ahead and booked it at a cost of 90,000 points total for three nights.

Over the last three years IHG ran a promo where it discounted many Caribbean properties by 50% during hurricane season. I knew it would likely come back this August, but even if it didn’t, I felt we were getting good value considering it’s a beachfront resort. And sure enough, the promo is back and you can take advantage of it if you book before the end of August. There is even one all-inclusive resort in Jamaica on the list, but you may want to read my review first.

Anyway, I was able to re-book my Holiday Inn stay in Aruba for only 15,000 points per night:

aruba discount booking

Unfortunately, only regular rooms with double beds were available (I have previously booked partial oceanview with king bed). Still, I felt that it was worth it to get a downgrade in order to save 45,000 IHG points. I also read that Platinum guests usually get upgraded, so I’ll take my chances. Either way, sleeping on two separate beds is not a deal breaker for my husband and I. In fact, he actually prefers it because he says I move around a lot during the night. I’m pretty restless even in my sleep.

The totals for our trip:

Flights: 38,000 Rapid Rewards points, plus $140 in taxes, paid with a gift card I got via Citi Prestige benefit.

Hotel: 41,500 IHG points (factoring in 10% refund). I have acquired them for around $140 total, which works out to $47 per night all-in. Not bad for an oceanfront hotel! Yes, we’ll have to pay for breakfast, but so what?

How you can pull off a similar trip


Flights: In all likelihood, you won’t be going to Aruba when the kids are in school. Fortunately, Southwest has connecting flights from various airports at a somewhat reasonable price. Here is an example from Newark during March, which is the height of Spring Break:

aruba new york

That’s less than 25,000 points roundtrip, which isn’t bad at all. With Companion Pass it’s a downright steal. If you have Chase Sapphire Preferred, Chase Sapphire Reserve or Chase Ink Plus, you can transfer Ultimate Rewards to Rapid Rewards points 1:1. If you are looking to apply for Southwest Airlines Rapid Rewards Premier Credit card,  you can use my personal referral link and get the following sign-up bonus:

  • Get 50,000 points  after you spend $2,000 on purchases in the first 3 months of opening your account.
  • You can also redeem 50,000 points for various gift cards, including Amazon and Walmart (50,000=$500 value)
  • Get 6,000 points after your Cardmember Anniversary
  • The annual fee of $99 is NOT waived.
  • Check for working direct and referral links on other Southwest card versions ( business card and Plus) in this Flyertalk thread.
  • Keep in mind that reportedly, this card is affected by Chase 5/24 rule. Also, you are only eligible for the bonus if you haven’t previously received it in the last 24 months.

Hotels: If you have four people, Holiday Inn resort in Aruba may not be the best fit because the rooms come with two double beds. For us, it’s a deal breaker, but some families will probably be OK with this type of set-up.  Of course, there is a decent chance of an upgrade with Platinum status that comes free with IHG co-branded card (read about it here), but it’s not a guarantee. If you have some flexibility on dates, you may want to consider participating in latest IHG Accelerate fall promo (see your offer here). And remember, kids eat free at all Holiday Inn resorts.

There are quite a few other chain hotels in Aruba, and the easiest way to see them all is via HotelHustle tool. Put in AUA in search ( a code for Aruba airport). If you are thinking about signing up for Chase Ritz-Carlton offer, you’ll be happy to know that there is a property  eligible for certificate redemption: The Ritz-Carlton Aruba It looks extremely nice, and rooms ((550 square feet!) come with two queen beds. Hat tip to Holly from ClubThrifty for mentioning it to me.

All in all, I’m quite excited about this trip. We’ll get to relax (truly relax since the kids won’t be there), check out new island and visit Netherlands…sort of.

Readers, is anyone else going to Aruba?

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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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9 thoughts on “Dumping Chicago for Netherlands (Sort of)

  1. IHG promotion. I have a one night paid stay booked at the Frankfurt Airport in September.
    One of my challenges is to stay one night in Sept and pay with my IHG credit card. which I did. but I booked it and paid for it a couple of months ago. Do you know if this will count or do you have any suggestions?
    As always, thank you for your help.

  2. @Hilde That’s a tough one. Another reader asked me the same question and I told her that I wasn’t sure. Calling IHG is usually pointless because most reps have no clue either. I didn’t see the requirement to book after registration cited in terms of promotion, but IHG may still try to weasel out of the bonus. If the rate is refundable, I would cancel and rebook the reservation. If it’s non-refundable, might as well keep it the way it is and hope for the best. Hopefully, it will track without any issues.

    • I checked the hotel and it cost now almost 2 x what I paid in February. Do you know if you have to book through their website for it to count or if you can just walk into a hotel and book a stay. I am toying with the idea of asking the hotel to rebook my stay when I get there, but don’t know if they will accept that.

      • @Hilde You might want to contact the hotel on the phone and see if they will rebook it for you at the same rate. I don’t know if it will work, but worth a shot. I know you can’t book it via third party (like Expedia or Orbitz), but if it’s done directly through hotel, it should be fine.
        Honestly, you may want to consider just leaving it as is. The terms specify that the stay has to occur during the dates of promotion. I don’t see anything about booking. As long as you are registered, it should be OK. Of course, if you want to play it safe, it won’t hurt to contact the hotel and see what they say.

  3. I’ll be curious about your thoughts on Aruba. I visited about 16 years ago as part of a week-long southern Caribbean cruise that left from Aruba. From what I remember, it was a very arid island and didn’t have that tropical jungle vibe that you find on many of the other islands in the Caribbean. It did have nice beaches. While sailing through the Netherlands Antilles, we also visited Bonaire and Curaçao, the latter which I found to feel the most “Dutch”.

    I know Aruba is outside the hurricane belt, but do you have a contingency plan if a hurricane is sitting over Florida on your return date?

  4. @Erik To be honest, Aruba wasn’t my first choice. I prefer islands that are lush and mountainous, which is why I love St. John and Kauai. I hesitated to book a trip to Aruba for that reason, but the more I did research, the more interesting and unique it looked. It will be neat to see a dessert on a Caribbean island.
    But more than anything, I’m looking forward to just relaxing with my husband: hot tub, pool, swimming in the ocean etc. Basically, a mindless vacation with lots of margarita drinks! 🙂 This hotel is close to the airport, so we’ll just hop into taxi, no car rental needed.
    As far as contingency plan if there is a hurricane in Florida, since Orlando is in the middle of the state, I believe we should be OK. It’s rare for that area to be affected to the point that they have to cancel flights. But if we are delayed, m in-laws will keep the kids an extra day or two. They are retired and live across the street from us. Obviously, I hope it doesn’t happen because my husband has to be back at work, but I’m sure his boss will understand.

  5. I’ve been to Curacao and it was a lot of fun. It’s not the lush tropical island, but the diving was amazing and the beaches were nice. I’m sure Aruba will be lots of fun. I’d just be happy for a kid-free getaway. Enjoy

    • @Jennifer I would love to visit Curacao! Unfortunately, Southwest doesn’t fly there. Having a non-stop route from Orlando or Tampa was crucial to me, as my husband hates flying and connections.
      I hope our trip goes well and we don’t argue too much! 🙂

  6. Pingback: So, We Missed our Flight to Aruba... - Miles For Family

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