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The best ways to fly to the Caribbean with miles

by on Mon June 19, 2017 • No Comment


The Caribbean is one of the most popular reward destinations, and while using your points for flights to the Caribbean won’t get you the big value you can get saving them for longer trips, there are plenty of ways to stretch your points and save money you can use for your hotel room.

Here are the best bets based on what points you have, or what airline you find most convenient.

Best bets with Chase, Amex, or Citi points

Chase Ultimate Rewards

If you have Chase Ultimate Rewards points that you want to use to fly to the Caribbean, here are the pockets of deals…

Flying Blue charges 30,000 miles to fly round trip in economy between the U.S. and the Caribbean on Delta. Interestingly, it costs a few less miles to fly from Hawaii to the Caribbean with Flying Blue – only 25,000 miles round trip in economy. If you’re going to Puerto Rico, Korean Skypass charges just 25,000 miles round trip in economy on Delta.

British Airways Avios can get you to the Caribbean for 15,000 – 25,000 points round trip if you fly nonstop American Airlines flights. Avios charges for awards per segment, which means trips with a connection cost more, so Avios are best if you live in an American Airlines hub like New York, Chicago, Dallas, Philadelphia, Miami, or Charlotte.

Here are a few routes and the number of Avios you would be charged:

  • Miami to Aruba – 15,000 points round-trip in economy
  • Miami to Montego Bay, Jamaica – 15,000 points round-trip in economy
  • New York to Cancun, Mexico – 20,000 points round-trip in economy
  • Chicago to Montego Bay, Jamaica – 20,000 points round-trip in economy
  • Dallas to Grand Cayman – 20,000 points round-trip in economy


The catch is award space on American is pretty spotty, so check for space before you transfer and trap your points in Avios.

Southwest is your other good value option if you’re flying on days when fares are low. Ultimate Rewards transfer to Southwest Rapid Rewards points at a 1:1 ratio, and Southwest is a great redemption option to the Caribbean we will go into full detail below.


If you want to fly United, a transfer to MileagePlus lets you get an economy seat for 35,000 miles, which is higher than the other options we’ve listed here.

American Express Membership Rewards

With Amex points, 30,000 Flying Blue miles for round trip Delta flights is one of the best redemption options for flights to the Caribbean, and Membership Rewards also transfer to Flying Blue at a 1:1 ratio.

If you live in an American Airlines hub, Amex points also transfer to British Airways Avios and let you book American Airlines flights. The transfer ratio is 1,000 Membership rewards to 800 Avios, so you can get flights for 18,750 – 25,000 Amex points if you’re flying on nonstop American Airlines flights.

If you live in Boston or New York, JetBlue points are also worth a try. Points transfer to JetBlue at a rate of 250 Amex points = 200 JetBlue points, so a 20,000 point JetBlue ticket costs 25,000 Amex points. JetBlue charges based on the cash airfare of the ticket, and if you fly when fares are low, you can often get flights for less than 25,000 Amex points.


JetBlue also has the most luxurious way to get down to the Caribbean, via its Mint service that features lie flat seats to Aruba, St. Lucia, Barbados, Grenada, and St. Maarten.

Citi ThankYou Points

As mentioned above, Flying Blue is one of the best redemption options for flights to the Caribbean, and ThankYou Points also transfer to Flying Blue at a 1:1 ratio.

Best options by airline



If you can score award space on a nonstop flight, British Airways Avios will usually be the cheapest for booking American Airlines flights. You’ll pay 15,000 – 25,000 Avios roundtrip in economy depending on the distance you fly, but remember Avios charges extra points for trips that involve a connecting flight.

With American AAdvantage miles you’ll pay at least 30,000 miles roundtrip, but won’t get charged extra for connecting flights.

Booked With Economy Class Price (Lowest) Business Class Price (Lowest)
Alaska Airlines 35,000 60,000
American Airlines 30,000 50,000
British Airways 15,000+ (distance dependent) 30,000+ (distance dependent)

delta air lines airplane


If you want to fly Delta, you have a lot of options in terms of good redemptions. Both Flying Blue and Korean Skypass allow redemptions on Delta for a reasonable number of miles. Flying Blue is a transfer partner of all of the major transferable points currencies and Korean Skypass is a transfer partner of Chase Ultimate Rewards.

Booked With Economy Class Price (Lowest) Business Class Price (Lowest)
Air France/KLM Flying Blue 25,000 – 30,000 60,000
Delta SkyMiles 35,000 – 40,000, Varies
Korean SKYPASS 25,000 – 35,000 45,000 – 75,000

Flying Blue prices are usually cheaper than Skypass (30,000 miles roundtrip versus 35,000 for Skypass), though if you’re heading to Puerto Rico Skypass charges only 25,000 miles. Flying Blue also lets you book one way awards for half the price of a round trip.

If you want to use Delta SkyMiles, the price can change anytime since Delta doesn’t publish an award chart anymore, but generally expect to pay 35,000 – 40,000 miles round trip for an Economy Class ticket if you plan ahead.



Southwest is a little different than the options listed above because the cost of Southwest flights in points is related to the cash price of a flight. This means if you look at a cheaper flight, it is going to cost less points than a more expensive flight. Another bonus is that Southwest allows every passenger to check two bags for free in addition to bringing a carry-on onboard.

Southwest is a 1:1 transfer partner of Chase Ultimate Rewards.

Southwest only serves nine destinations in the Caribbean at this time:

  • Aruba
  • Punta Cana, Dominican Republic
  • Grand Cayman
  • Havana, Cuba
  • Santa Clara, Cuba
  • Varadero, Cuba
  • Montego Bay, Jamaica
  • Nassau, Bahamas
  • San Juan, Puerto Rico

Since the price of a Southwest flight in points is related to the cash fare, you will need to look up the prices for your own origin, destination, and travel dates, but we will list a few data points to give you an idea of pricing.

Generally, the best prices for Southwest flights to the Caribbean are from the East Coast and Southeast, and the worst prices are from the Midwest and Northwest.

Here are some example prices from the time of researching this article. Note that these exact prices may not be available anymore.

Route Price (Round Trip) When
Newark – San Juan 19,512 Tuesdays in October
LAX – San Juan 22,176 Very limited dates October – November
Atlanta – Punta Cana 21,312 Fall 2017
Houston – Aruba 21,456 Fall 2017
Seattle – San Juan 31,284 Fall 2017

Overall, these prices are more competitive than even the best of the other options, with the exception of redeeming British Airways Avios for short flights on American Airlines.

Since Southwest prices are based on the fare, watching for Southwest fare sales will mean watching for lower points prices too.



If you are set on flying United on your way to the Caribbean, Singapore Krisflyer and United MileagePlus have the lowest mileage prices for United flights to the Caribbean, at 35,000 miles round trip for Economy and 60,000 miles for Business Class.

Membership Rewards can transfer to Air Canada Aeroplan, which lets you book United flights, but Aeroplan charges 40,000 miles for an Economy Class ticket.

Booked With Economy Class Price (Lowest) Business Class Price (Lowest)
Air Canada Aeroplan 40,000 60,000
Singapore Krisflyer 35,000 60,000
United MileagePlus
35,000 60,000

What’s best?

The best redemption is going to depend on what miles you have available and what the airline availability is like during the time you want to travel. Assuming you have all of the options available to you, if you are flying from an American Airlines hub to the Caribbean, redeeming British Airways Avios is a great option.

If Southwest can get you there, and you have Chase or Southwest points, there’s a good shot it’s your best option.

In the absence of those options, Flying Blue is the the third best option, unless you are flying to Puerto Rico, then Korean if your best bet.

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Chase Sapphire Preferred® Card

Miles dont expireas long as card is open
Learn more

Partner Offer

50,000 bonus points

Intro Offer

$0 introductory annual fee the first year, then $95

Annual Fee


Foreign Transaction Fee Waived

Yes - transfer to United MileagePlus, Southwest Rapid Rewards, Marriott Rewards, and more

Points Can Transfer to Airline Miles ?

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