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TravelBest ways to book flights to the Caribbean using points and miles

Best ways to book flights to the Caribbean using points and miles


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.

Related: 8 best overwater bungalows in the Caribbean

Best US airlines to fly to the Caribbean

ZACH GRIFF/THE POINTS GUY

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.

Related: American adds 2 new Caribbean routes, goes up against Delta, 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:

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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’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.

Related: How to book award flights using British Airways Avios

Book flights to the Caribbean on Delta Air Lines

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.

Any time you’re booking a Delta flight, you should always consider starting your search on Virgin Atlantic Flying Club’s website instead. Not only are both airlines transfer partners of American Express Membership Rewards, but Virgin Atlantic will often charge you fewer miles for Delta flights than Delta will (Virgin and Delta are partners as SkyTeam members).

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.

VIRGINATLANTIC.COM

Related: Unlock incredible value with Virgin Atlantic Flying Club

Book flights to the Caribbean on United Airlines

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.

Related: Fly or sail: Your guide to traveling between St. Martin and Anguilla

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.

Related: How to quickly earn the Southwest Companion Pass

Book flights to the Caribbean on JetBlue

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.

JETBLUE.COM

Related: How to earn points with the JetBlue TrueBlue program

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.
  • Bilt Rewards: American Airlines (transfer partnership ends in June), British Airways and Virgin Atlantic have 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 credit 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: Earn 80,000 Membership Rewards points after you spend $8,000 on purchases on your card in your first six months.
  • Capital One Venture Rewards Credit Card: Earn 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening.
  • Chase Sapphire Preferred® Card: Earn 75,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.
  • Chase Sapphire Reserve®: Earn 75,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.
  • Capital One Venture X Rewards Credit Card: Earn 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening.
  • The Business Platinum Card® from American Express: Earn 150,000 Membership Rewards points after you spend $20,000 in eligible purchases within the first three months.
  • Citi 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.

Related: Best travel credit cards of 2024

Bottom line

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.

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