Maximizing Chase Ultimate Rewards for Trips to the Caribbean

Update: Some offers mentioned below are no longer available. View the current offers here.

In August, Chase introduced a fantastic new credit card that quickly became a sensation: the Chase Sapphire Reserve. The card is currently offering a sign-up bonus of 100,000 Ultimate Rewards points after you spend $4,000 on purchases in the first three months from account opening. This sign-up bonus is worth at least $1,500 when you redeem the points directly for travel, but you can get even more value by transferring them to partners like Hyatt and United. Today I’ll continue my series that highlights how this sign-up bonus can get you to specific destinations. I started by looking at a trip to Hawaii and then took a look at domestic travel, and now I'll consider how to get to the Caribbean.

Before getting into specifics of how you can reach the Caribbean, here’s a quick reminder of how I’ll approach this series. For starters, I’ll be looking primarily at transferring these points to partners as opposed to booking travel directly. This tends to be where you can get outsized value from your Ultimate Rewards points. In addition, I’ll assume that you spent $3,000 on travel and dining purchases and $1,000 on everyday purchases to meet the minimum spending required for the sign-up bonus. This will leave you with 110,000 Ultimate Rewards points.

Finally, I’ll break this down by flight and hotel, both of which tend to be the largest expense of a vacation. If there’s more than one option for each, I’ll include that as well. Note that in some cases, you’ll be able to book two round-trip tickets, but if you have your eye on first or business class, chances are you’ll only be able to book a single ticket (if that).

Keep in mind too that these suggestions only apply to a single individual opening the Sapphire Reserve. If you’re looking to travel with a spouse, significant other or family member, it could make sense for you both to open the card. There’s also the Chase Sapphire Preferred Card and the brand-new Ink Business Preferred Card, both of which can further boost your Ultimate Rewards account balance. You also have many other credit cards that can further enhance your trip. I’ll try to highlight those options where they apply, though keep in mind Chase’s 5/24 rule as you plan out your card application strategy.

With that all out of the way, let’s take a look at how the Chase Sapphire Reserve can help with your travels to the Caribbean!

FLIGHTS

Option 1: Transfer points to British Airways

One of the best ways to utilize Ultimate Rewards points for flights to the Caribbean is by transferring your points to British Airways. Thanks to the carrier’s distance-based award chart, you can book round-trip award tickets for as little as 15,000 Avios on partner American Airlines. This used to be even more lucrative until the 4,500-Avios option was eliminated in North America, but it still unlocks the following redemptions:

• One-way flights of up to 1,151 miles (like Miami to San Juan, Puerto Rico): 7,500 Avios
• One-way flights of up to 2,000 miles (like Charlotte to Curaçao): 10,000 Avios
• One-way flights up up to 3,000 miles (like Los Angeles to Montego Bay, Jamaica): 12,500 Avios

With American hubs in Miami, Charlotte and Dallas-Fort Worth (among others), this opens up a large swath of the Caribbean for relatively few miles. For example, here's a map highlighting those destinations within 2,000 miles of Miami International Airport:

As you can see, you can access the entire Caribbean for just 20,000 Avios round-trip, making this a fantastic option for Florida-based travelers like me. My wife and I actually booked nonstop flights from Miami to Curaçao for a friend's wedding back in 2014 by transferring Ultimate Rewards points to British Airways. Revenue flights were more than $800 apiece, so we got nearly 4 cents of value per point.

While the British Airways search engine does show American award flights, I have found that the inventory doesn't always match what's on AA.com. As a result, I'd use both sites to confirm availability and then call if you can't find the flights you want through BritishAirways.com. This is also where you can use ExpertFlyer to search award inventory (or even set alerts) ahead of time so you’ll know when flights are available.

Option 2: Transfer points to Southwest

Another option for flights to the Caribbean is Southwest. While the carrier is probably most known for its domestic operations, it has been expanding its international service rather quickly over the last few years, and you may not even be aware of some Southwest destinations. One of its biggest Caribbean destinations is Cancun, with nonstop flights from several domestic gateways, including Baltimore-Washington (BWI), Denver (DEN), Chicago-Midway (MDW), Atlanta (ATL), San Antonio (SAT), Austin (AUS) and Houston-Hobby (HOU).

While the Rapid Rewards program is revenue-based, Southwest still offers a pleasant experience and points can be worth up to 1.9 cents apiece on Wanna Get Away fares (TPG pegs them at a more conservative 1.5 cents apiece in his most recent valuations). I have many friends and family members who love Southwest thanks to its free checked bags and waived change and cancellation fees, and the beauty of the Rapid Rewards program is its relative simplicity: If there’s a seat available for sale, you can redeem points for it. The pricier that seat is in dollars, the pricier it will be in points.

You can use a couple methods to extend the value of your points even further. First, you can maximize your redemptions by taking advantage of the carrier’s no change fee policy. If the price of your award ticket drops after you book it, you can exchange that ticket for free and receive the point differential back into your account. More importantly, you can get a ton of value out of the program if you can earn the Companion Pass. This perk allows you to bring a companion for free on all Southwest flights, including both paid and award tickets. You can even get it for almost two years if you time it right!

Note: The sign-up bonus on the Southwest Rapid Rewards Premier Credit Card can help improve your chances of snagging a Companion Pass, but note that transfers from Ultimate Rewards do not count toward Companion Pass qualification.

Option 3: Transfer points to Flying Blue

A third option for flights to the Caribbean is the newest partner of Chase Ultimate Rewards: the Flying Blue program of Air France and KLM. Since both carriers belong to Sky Team, you can redeem Flying Blue miles for flights on Delta, and award tickets to the Caribbean start at just 25,000 miles round-trip. While Delta no longer publishes award charts, award flights from the US to the Caribbean through the SkyMiles program start at 35,000 miles round-trip (the same price you'd pay by transferring points to Korean as well).

Summary

As you can see, the Ultimate Rewards program gives you many options for transferring points to partners that then allow redemptions on flights to the Caribbean. While there are other options for these award tickets, they don't offer the same value as the three listed above.

HOTELS

Option 1: Transfer points to Hyatt

One of my favorite Ultimate Rewards transfer partners is Hyatt Gold Passport, and you have several properties across the Caribbean at which you can redeem your points. The best part of this value proposition is the relatively low number of points you’d need for these properties:

• Hyatt Regency Trinidad: Category 4 (15,000 points per night)
• Grand Hyatt Playa Del Carmen: Category 5 (20,000 points per night)
• Hyatt Regency Aruba Resort Spa and Casino: Category 6 (25,000 points per night)
• Hyatt Ziva Cancun: Category 6 (25,000 points per night)
• Park Hyatt St. Kitts: Category 7 (30,000 points per night)

While this list certainly doesn't cover every island in the Caribbean, it still gives you some nice options from which to choose. Keep in mind too that this doesn’t even consider the program’s Points + Cash awards.

Note: The Hyatt Credit Card could be a nice pairing here, as it’ll give you two additional free nights with the current sign-up bonus.

Option 2: Transfer points to Marriott

Another option for free Caribbean hotel stays through Ultimate Rewards is by transferring to Marriott Rewards. This generally becomes a particularly attractive option at the middle and high categories in the program, as you can book properties like the Renaissance Curaçao Resort & Casino for just 25,000 points per night. In addition, since you can now link your Marriott account with your SPG account, you can actually convert your Ultimate Rewards points to Starpoints by first transferring to Marriott and then to SPG (though at a paltry ratio of 3 Marriott points: 1 Starpoint). While this isn't the best option for top-tier properties, you do have some lower-category SPG properties in the Caribbean, especially in Puerto Rico and the Dominican Republic.

In some cases you could come out ahead by booking a revenue stay directly through Ultimate Rewards at 1.5 cents per point (assuming you have the Reserve card), so be sure to confirm paid rates before initiating a transfer. Also, just like with Hyatt, you have Cash + Points awards to utilize, and the program also allows you to make award reservations even when you’re short on points. This can allow you to lock in a pricier redemption for a stay way into the future and then build up your Ultimate Rewards (or Marriott Rewards) balance leading up to the stay.

Note: The Marriott Rewards Premier Credit Card could help here, thanks to its sign-up bonus and automatic Silver status (with an option to “buy up” to Gold).

SAMPLE ITINERARIES

Option 1:
Flight: Two round-trip, nonstop flights on American Airlines from Miami (MIA) to Curaçao (CUR) using British Airways Avios
Hotel: Three nights in the Renaissance Curaçao Resort & Casino
Total cost: 105,000 Ultimate Rewards points

Option 2:
Flight: ~$450 worth of flights on Southwest to Cancun
Hotel: Four nights at the Grand Hyatt Playa Del Carmen
Total cost: 110,000 Ultimate Rewards points

Option 3:
Flight: Two round-trip flights on Delta using Flying Blue miles
Hotel: Four nights in the Courtyard Bridgetown, Barbados using Cash + Points
Total cost: 106,000 Ultimate Rewards points + $260

Option 4:
Flight: Four round-trip, nonstop flights on American Airlines to Cancun (CUN) using British Airways Avios
Hotel: Five nights at the Grand Hyatt Playa Del Carmen using Points + Cash
Total cost: 110,000 Ultimate Rewards points + $625

Bottom Line

Traveling to the Caribbean can be a bit challenging for points and miles enthusiasts, as your hotel options for redemptions are relatively limited. Nevertheless, there are still some great ways to maximize the sign-up bonus on the new Chase Sapphire Reserve Card to get there, and the best part is that you don't have to commit to a single airline or hotel chain. This is one of the main reasons why it’s critical for all travelers to have transferable points. Hopefully this post has given you some strategies for planning a trip down to the tropics, especially for all our Northern readers gearing up for winter!

How would you book a trip to the Caribbean using the points from the Sapphire Reserve?