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Our site may earn compensation when a customer clicks on a link, when an application is approved, or when an account is opened with our partners, and this may impact how or where these products appear. While we don't cover all available credit cards, our editorial team creates and maintains all of the analysis of these cards, and our content is not influenced nor subject to review by any credit card company, bank or partner prior to (or after) publication. Please view our advertising policy and product review methodology for more information.
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Best ways to book flights to the Caribbean using points and miles
Ethan's been a frequent flier for as long as he can remember, from studying abroad in Paris to moving to Shanghai after graduating college, where he served as TPG's eyes and ears for all things travel in the Asia-Pacific region. If you asked him where he wants to travel next he'd quote Anthony Bourdain and tell you "anytime I'm eating spicy noodles in a bowl, I'm happy."
Ben Smithson is a senior writer for TPG and is based in London. Originally from Australia and a qualified lawyer with a financial services background, he has almost a decade of experience writing about a broad range of travel and loyalty topics.
also contributed to this story
May 2, 2024 • 11 min read
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By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
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Quick summary
The article explores the best ways to book flights from the U.S. to popular Caribbean destinations using airline loyalty programs.
It compares redemption options across several major U.S. airlines, highlighting both fixed and dynamic award pricing models.
Transferable points from various rewards programs can be used to access partner airlines for potentially better redemption rates.
Seasonal schedules and hub cities play a significant role in route availability and award pricing.
What to consider
Award pricing varies widely by airline, route and travel dates, with dynamic pricing often leading to fluctuating redemption rates.
Some loyalty programs offer better value through partner bookings, but additional connections may increase the points required.
Transfer ratios and partnerships between rewards programs and airlines differ, so review current terms before transferring points.
What you'll miss from the article
A detailed breakdown of which airline and loyalty program combinations offer the best value for specific Caribbean routes.
Generated by AI with support from our editorial team.
Update: Some offers mentioned below are no longer available. View the current offers here.
There are undeniably pros and cons to living on either coast of the United States. While the West Coast has relatively easy access to Hawaii, a perk of living on the East Coast is the seamless ability to visit many tropical destinations in the Caribbean.
It's especially tempting to get away during the wintertime in the north to shake off the cold and escape to a tropical paradise. Depending on where you're located on the East Coast, in just a few hours, you can be lying under a palm tree, sipping on something fruity.
You’ll find plenty of flights from all over the U.S. to various Caribbean islands, and we’re going to look at the best ways to get there using points and miles.
While there are over 7,000 islands in the Caribbean, we will focus on the most popular tourist destinations — the islands with the best points hotels — and the islands with regular air carrier service. These are:
Grand Cayman
Aruba
St. Martin
U.S. Virgin Islands
Bahamas
Turks and Caicos
St. Kitts
Many of these islands feature local carriers like Bahamasair or Cayman Airways, but we will focus here on the U.S. airlines that make it easy to redeem points and miles on these routes, specifically United Airlines, American Airlines, Delta Air Lines, Southwest Airlines and JetBlue.
With seven destinations, five different airlines and seasonal schedules, it’s too complicated to list every single route these carriers fly, but flights to the Caribbean are primarily based out of East Coast and Southeast hub cities. If you live in one of these cities, you may even be able to enjoy nonstop routes. Otherwise, expect to connect through one of these airports:
Airline
Hub airports
American
Miami International Airport (MIA)
Charlotte Douglas International Airport (CLT)
LaGuardia Airport (LGA)
Dallas Fort Worth International Airport (DFW)
O'Hare International Airport (ORD)
Delta
Hartsfield-Jackson Atlanta International Airport (ATL)
John F. Kennedy International Airport (JFK)
United
Newark Liberty International Airport (EWR)
George Bush Intercontinental Airport (IAH)
Southwest
Fort Lauderdale-Hollywood International Airport (FLL)
JetBlue
Fort Lauderdale-Hollywood International Airport (FLL)
John F. Kennedy International Airport (JFK)
Boston Logan International Airport (BOS)
This is not an exhaustive list, and note that routes may be seasonal to reflect tourist demand.
How to book flights to the Caribbean using points and miles
Book flights to the Caribbean on American Airlines
The American Airlines AAdvantage award chart shows that one-way flights from the U.S. to the Caribbean start at:
Economy: 10,000 AAdvantage miles
Business: 20,000 AAdvantage miles
While these are starting prices, and on peak dates they may be much higher, you can use the calendar search on American's website to check which dates are available at these prices. Here's a flight from Miami to St. Kitts' Robert L. Bradshaw Airport (SKB):
AA.COM
If you have Alaska Airlines Mileage Plan miles, you can also book American Airlines flights to the Caribbean at low prices in economy class. Flights up to 700 miles in length (like short hops to the Bahamas) cost just 4,500 miles, with flights of 701 to 1,400 miles costing 7,500 miles. Even flights up to 2,000 miles in length, covering even the farthest American Airlines flights from Miami to the Caribbean, are priced at 12,500 Alaska miles.
If you’re originating in Miami and looking for fixed pricing, these short hops also offer phenomenal value when booked with British Airways Avios. You can still book awards from Miami to many Caribbean destinations for only 8,250 Avios each way in economy for flights up to 650 miles long, or 11,000 Avios for flights 651-1,152 miles long.
Match this deal with one of the frequent transfer bonuses to British Airways, and this deal gets even better. Note that the distance-based award chart will make your trip more expensive if you add a connecting flight to Miami because British Airways charges per leg.
Plus, American Airlines is doubling its daily nonstop flights between Miami and St. Lucia's Hewanorra International Airport (UVF) starting June 5, giving you even more ways to fly to the Caribbean with AAdvantage miles or Avios.
Delta SkyMiles’ dynamic award pricing makes it hard to speak generally about how much an award ticket should cost, as prices fluctuate daily to match demand. For most of the schedule, 17,000 miles each way appears to be the lowest price for economy awards to the Caribbean (39,000 miles for business class), which is generally higher than other programs charge, so this may not be the best program to use when looking to book flights to the Caribbean.
At 11,000 miles each way, Virgin Atlantic’s pricing between Atlanta and Nassau's Lynden Pindling International Airport (NAS) is 6,000 miles cheaper than booking through Delta for the same flight.
United Airlines has the most limited Caribbean route network of the major U.S. carriers, flying predominantly out of Newark (EWR). United uses dynamic award pricing, but it’s still possible to find pricing as low as 16,800 MileagePlus miles each way for economy flights from Newark to St. Martin's Princess Juliana International Airport (SXM). This is slightly cheaper than the lowest price we found through Delta SkyMiles, but not by much.
UNITED.COM
You can use the 30-day calendar feature to find the lowest prices across various dates.
Book flights to the Caribbean on Southwest Airlines
Southwest Rapid Rewards uses a revenue-based award chart, so the number of points you’ll need depends on the cash price of the ticket, and your points will usually be worth about 1.4 cents each.
Much of Southwest’s great reputation was built on low fares, and it’s still possible to find one-way awards from the U.S. to the Caribbean for only 9,877 points or potentially even less, as we found from Fort Lauderdale to Nassau. Almost all of Southwest’s Caribbean flights connect through Fort Lauderdale (some go through Orlando), so plan for a layover.
SOUTHWEST.COM
These cheap flights would also be a great time to use the Southwest Companion Pass, which can drop the cost of your tropical vacation as it allows your dedicated plus-one to fly for free (plus taxes and fees). Therefore, in this example, you can pay just under 10,000 points for two people to fly to the Caribbean (excluding taxes and fees), which is much cheaper than most legacy carriers would charge.
JetBlue's TrueBlue program follows the same revenue-based approach to redemptions, tying its award rates directly to the cash cost of the ticket. If you’re flexible with your dates and/or willing to stop on the way, you can find one-way awards starting as low as 9,300 TrueBlue points, such as from New York to Aruba's Queen Beatrix International Airport (AUA).
JETBLUE.COM
JetBlue stands out above the crowd here thanks to its Mint business class, which you can find on select flights from Boston and New York to the Caribbean (you can check where Mint is currently offered here). Mint features fully flat seats on an Airbus A321, including four "throne" seats with closing doors. Yes, you read that correctly — private suites on a narrow-body aircraft.
Mint tickets are significantly more expensive than JetBlue’s economy awards, but it might be worth paying up to experience the best premium cabin in North America.
While many of these airlines now use dynamic pricing for redemptions, there are plenty of great deals you can snag. Plus, if you have transferable credit card points, you can utilize transfer partners to find the best-priced flight to suit your travel plans. Check out which credit card partners you could use to book a flight to the Caribbean:
American Express Membership Rewards: British Airways (which can be used to book American Airlines flights), Delta and Virgin Atlantic (which can be used to book Delta flights) have a 1:1 transfer ratio; JetBlue has a 250:200 transfer ratio.
Capital One miles: British Airways and Virgin Red (which can be used to book Delta flights) have a 1:1 transfer ratio.
Chase Ultimate Rewards: British Airways, JetBlue, Southwest, United and Virgin Atlantic have a 1:1 transfer ratio.
Citi ThankYou Rewards: Virgin Atlantic has a 1:1 transfer ratio.
Wells Fargo Rewards: British Airways has a 1:1 transfer ratio.
Best travel credit cards to book a trip to the Caribbean
BEN SMITHSON/THE POINTS GUY
Moving points from transferable points programs is a good strategy to boost your airline points and miles balances.
Here are some of the best travel cards offering strong welcome bonuses right now, whether you are looking to earn points and miles to book flights to the Caribbean or to spend on cash airfares or associated travel costs like accommodation and dining while you are in the Caribbean:
The Platinum Card® from American Express: Find out your offer and see if you are eligible for as high as 175,000 bonus points after you spend $12,000 on purchases on your card in your first six months. Welcome offers vary, and you may not be eligible for an offer.
Capital One Venture Rewards Credit Card: Earn 75,000 bonus miles after spending $4,000 on purchases within the first three months from account opening.
Chase Sapphire Preferred® Card (see rates and fees): Earn 75,000 Ultimate Rewards points after you spend $5,000 on purchases in the first three months of account opening.
Chase Sapphire Reserve® (see rates and fees): Earn 125,000 bonus points after spending $6,000 on purchases in the first three months from account opening.
Capital One Venture X Rewards Credit Card: Earn 75,000 bonus miles after spending $4,000 on purchases in the first three months from account opening.
The Business Platinum Card® from American Express: Find out your offer and see if you're eligible for as high as 300,000 bonus points after spending $20,000 on purchases in the first three months of card membership. Welcome offers vary, and you may not be eligible for an offer.
Citi Strata Premier® Card (see rates and fees): Earn 60,000 bonus ThankYou points after you spend $4,000 on purchases within the first three months of account opening.
Wells Fargo Autograph Journey℠ Card (see rates and fees): Earn 60,000 bonus points when you spend $4,000 on purchases in the first three months.
There are many different ways to fly from the U.S. to the Caribbean, and the amount of competition means there are great deals to be had if you want to redeem your points and miles. While these are technically international flights, the short distances and narrow-body jets operating them can feel more like domestic travel within the U.S.
No matter which airline you earn your miles with, you should be able to find a good option for flying to the Caribbean — but remember to always check cash prices before transferring your miles.
Comments
By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
