Chase Credit Card Points: My Epic $3,200 All-Inclusive Caribbean Vacation. Here’s How You Can Do It Too

September 7, 2019 By Devon O'Rourke

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INSIDER SECRET: Chase Ultimate Rewards points are our team’s favorite way to book both regular and luxury travel. With plenty of transfer partners and valuable redemption options, having a card like the Chase Sapphire Preferred® Card could have you booking your own $3,200 vacation for next to nothing — like me.

I’m about three years into this miles and points hobby and I just came back from my first epic vacation (which happily doubled as my honeymoon). It cost me next to nothing, and was valued around $3,200. That’s unreal.

I used Chase credit card points, my Southwest Companion pass and some other perks to make this trip a reality.

Chase Credit Card Points: My Epic $3,200 All-Inclusive Caribbean Vacation. Here’s How You Can Do It Too — My Chase credit card points let me take an epic $3,200 vacation to Jamaica for next to nothing. (Photo by Devon O’Rourke/Million Mile Secrets)

Chase Credit Card Points and How to Use Them for Epic Value

My $3,200 honeymoon was mostly taken care of by using Chase credit card points, my Southwest Companion pass, the Hilton Honors Aspire Card from American Express and some other perks.

The basics of our trip:

We flew Southwest to Montego Bay, Jamaica.
We used our Priority Pass to access a lounge during a layover in Orlando, Florida.
When we landed in Jamaica, we took a shuttle to the Hyatt Zilara all-inclusive resort and stayed for five nights.
We flew Southwest to Baltimore, Maryland and tried to visit a lounge during our layover, then finally made it home

The information for the Hilton Aspire card has been collected independently by Million Mile Secrets. The card details on this page have not been reviewed or provided by the card issuer.

Hyatt Zilara Rose Hall – All Inclusive Adult Resort

The Hyatt Zilara Rose Hall is an adult-only resort in Montego Bay that shares a border with the Hyatt Ziva resort (where kids under 21 are allowed). As an adult, you have access to both resorts.

When we arrived in our shuttle, we were greeted with glasses of champagne and prompt service by the front desk, then driven by golf cart to the building where we’d be staying. Unfortunately, the only upgrade we were offered was for $100 extra per night. I declined, but I imagine if I had the right Hyatt status I would have been offered that upgrade for free.

Our room was clean and well stocked with toiletries and beverages every day. The resort was clean and not too busy. The food was spectacular — so much so that we went to two different restaurants for dinner on the same night just to try all the options (our bodies weren’t too happy). Bartenders and servers kept the drinks flowing and would drop off water bottles, too. I really liked that they tried to keep folks hydrated.

All the basics were free but we tipped about $1 per drink and for “fast food” and $5-$10 for sit-down dinners and other services like shuttle and luggage handling. Some folks didn’t tip and others tipped much more than us. The hotel has an official policy that tipping is not required. Most bartenders and waitresses were very grateful for the tips, and folks like bellhops and shuttle drivers seemed to expect them.

We’d probably opt for a less energetic resort next time as the entertainment could get loud at times, but overall, we loved the experience and were very happy with the resort.

I recently missed out on a dream trip to Hawaii because I didn’t plan accordingly or early enough — so I began the planning for this trip well in advance.

I used 125,000 Chase Ultimate Rewards points for the hotel stay, which I earned using my Chase Sapphire Preferred, the perfect card for a beginner. I transferred those directly to Hyatt and booked the room through the Hyatt website. There were no extra fees.

The cash value of my hotel stay was ~$2,200 but could swing as high as ~$2,600 and as low as ~$1,700 for five nights depending on the time of year and availability.

Chase points are valued at 1 cent each for cash back, 1.25 cents each when redeemed through the Chase Travel Portal, and anywhere from 0.3 and 6 cents each when you transfer to a travel partner. I got ~1.76 cents per point for my redemption through Hyatt, ($2,200/125,000 points). Transferring to Hyatt is an easy way to redeem Chase points for 1.5-2 cents per point. That’s far more than you can typically get by transferring other hotel brands.

I wouldn’t do much different in hindsight. Maybe I’d use the $300 annual travel credit the Chase Sapphire Reserve offers to offset the shuttle fee of $30 per person round trip, or get the World of Hyatt Credit Card for some Hyatt points and the Discoverist status that comes with the card, but I’m waiting until I get under the Chase 5/24 rule before applying for these cards.

Southwest Flights and The Southwest Companion Pass

I earned over 110,000 Southwest Rapid Rewards points by meeting minimum spend requirements on both the Southwest Rapid Rewards® Plus Credit Card and the Southwest Rapid Rewards® Premier Credit Card. Thanks to the help of those two bonus I earned the coveted Southwest Companion pass. (Note: The amount of points required to obtain the Companion Pass has increased to 125,000 points in a calendar year)

Booking and canceling flights with Southwest has to be the easiest user experience out there. When you’re booking a flight with the intention of adding a companion, make sure there are at least two seats left on your flight or you won’t be able to add your companion until another seat opens up.

You can see below that after I originally booked my flight I found a cheaper itinerary out of a nearby airport. So I cancelled that flight and rebooked to save ~15,000 points. It doesn’t get any easier than that.

Since this was an international flight, I needed to pay $142 per person in taxes and fees on top of the 30,732 points for one of the tickets (remember, the second fare didn’t cost any points because of the Southwest Companion pass). I had applied for the Amex Hilton Aspire last year and used the $250 airline incidental credit to purchase Southwest gift cards — which is not technically a qualifying incidental charge (Southwest gift card purchases will no longer trigger Amex airline credits) but I was reimbursed through statement credits. With that move, it really only cost me $34 out of pocket for the fees ($284 – $250 gift card). The tickets were valued at $922.

My companion pass expires at the end of this year. I’m still not sure If I’ll pursue another two years of this amazing deal because I’ve got my eyes set on the Ink Business Preferred Credit Card and the Ink Business Cash Credit Card so I can earn more Chase Ultimate Rewards points and those cards have better earning structures for me, plus Southwest doesn’t have many nonstop routes out of my airport. That said, the Southwest Rapid Rewards Performance Business Credit Card is offering 80,000 points after you spend $5,000 on purchases in the first three months of account opening. That would make it fairly easy to reach the 125,000 points needed for the Southwest Companion pass.

If Southwest flies out of a airport and you often fly with a companion, I’d recommend pursuing the Companion Pass because it’s a no-brainer and super easy to use.

Lounge Access Using Priority Pass

During our layovers in Orlando and Baltimore, we had the opportunity to visit some Priority Pass lounges for free meals, WiFi and more.

My Amex Hilton Aspire comes with a free Priority Pass membership, which gets me, and two guests, unlimited lounge visits. If I paid for a Priority Pass membership with unlimited visits it would cost me $429 per year and I’d still have to pay $32 per guest. I’d say we got $40-$80 in value out of our lounge visits.

In Orlando, you don’t have to go through security to transfer terminals so it was really easy to get to the MCO2 Lounge. There was a buffet with hot breakfast, a top-class coffee machine and amenities like free WiFi and a super clean restroom. The bar was open and well stocked with specials to make your breakfast experience superb. We each got two specialty coffees, a full breakfast and a mimosa before departing. The service and cleanliness of this lounge helped put us in a great mood for our next flight.

In Baltimore on the return leg we missed out on The Club BWI in Concourse D. Our flight into Baltimore was delayed, plus we had to pass through customs and would have needed to re-enter security at both Concourse D and B, where our flight was. We decided it wasn’t smart to risk the visit, so we missed out on a free dinner and drinks.

There are a bunch of cards that offer lounge access and Priority Pass membership. We’ve got a full breakdown of the best cards with lounge access; our team’s favorite is the Chase Sapphire Reserve.

Bottom Line

It took me a while to plan and execute my $3,200 dream honeymoon vacation but it was well worth it.

By maximizing my Chase points, the Southwest Companion pass, the Amex Hilton Aspire and some other perks I was able to fill my belly with a lot of free food and spend time under the sun in Jamaica with my new wife.

I hope you can pick out the parts of my trip that relate to you and use it to plan your own unforgettable vacation.

Check out the below posts for more information on how to use and earn Chase Ultimate Rewards points:

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