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:

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:

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?

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