Ultimate Guide to Using Points and Miles for Flights to the Caribbean

The Caribbean is one of the most popular travel destinations for North Americans seeking a getaway to enjoy beautiful beaches and warm weather most of the year. Numerous flight options, bookable with points and miles, add to the region’s appeal.

Although there are numerous geographic and airline-defined boundaries for the Caribbean, we’re focusing on islands that are considered to be part of North America and are located between the southeastern part of the mainland United States, Mexico, Central America and South America. This includes U.S. territories – Puerto Rico and the Virgin Islands – and islands as far north as the Bahamas and as far south as Trinidad and Tobago. We’re not including Mexico or Central America when discussing the Caribbean.

Traveling to the Caribbean presents some challenges and decisions for people who are interested in using points and miles for flights. The Caribbean is primarily a leisure destination, and the majority of visitors to many Caribbean islands are traveling from the United States, on relatively short duration flights.

Traditionally, U.S.-based airlines have treated flights to the Caribbean like domestic destinations in terms of planes used and service standards. This changed somewhat during 2020 and 2021, when airlines weren’t operating many long-haul international routes and redeployed some internationally configured planes to Caribbean routes.

Given that the Caribbean is a leisure destination with seasonal fluctuation in demand, prices for paid flights vary significantly. Fare sales for round-trip economy travel, including taxes and fees, sometimes result in prices from the U.S. being around $300, but the same route may cost well over $1,000 during higher demand periods. Caribbean destinations that aren’t U.S. territories often have round-trip taxes and fees ranging from about $60 to over $150. Traveling during off-peak or shoulder seasons and selecting destinations with lower taxes and fees can have a big impact on flight cost.

If you’re thinking “I’m going to use points and miles for flights to the Caribbean, so I don’t care about paid flight prices,” it’s important to recognize that award flights from the U.S. are impacted by paid flight prices, since many U.S. airlines flying to the Caribbean price awards dynamically. We’ll dive into the details about this.

Another question you should consider is whether premium cabin flights are worth the additional cost on Caribbean routes. This is a personal decision, so we’re sharing information about both premium cabins (business or first-class) and economy awards. Many nonstop flights from the continental U.S. to the Caribbean are between two to four hours long and are on planes that don’t have lie-flat seats or offer international business class service.

Airlines Operating Flights to the Caribbean

Although we’re focusing on U.S. to Caribbean travel, there are nonstop or direct flights to the Caribbean from other regions too.

Travel from the United States

Most currently available service between the Caribbean and the continental U.S. is on the following airlines:

• American Airlines
• Delta Airlines
• JetBlue
• Southwest Airlines
• United Airlines.

For that reason, we’re focusing on these airlines, their loyalty programs and selected partner programs that can be used to book flights on these airlines. Deciding which partner programs are best for booking Caribbean flights depends on the specific itinerary and the types of miles you have or can obtain.

Low-cost or regional airlines also offer U.S. to Caribbean service, but these airlines are less valuable for award travel, since they either don’t have loyalty programs with points or miles that can be earned easily, or they don’t partner with other airlines or bank flexible currency programs to enable booking flights using other points or miles currency. Airlines in this group include BahamasAir, Cayman Airways, Frontier Airlines, Silver Airways (aka Seaborne Airlines), Spirit Airlines, and Sun Country. Silver Airways partners with major U.S. airlines, including American, JetBlue (earning only) and United, but there is rarely award availability on flights that Silver operates.

Travel from Other Regions

If you’re traveling between the Caribbean and Canada, Air Canada is the primary major airline with an affiliated loyalty program, Aeroplan, that can be used to book award flights.

From Europe, nonstop service is more limited and generally aligns with current or previous political relationships between Caribbean destinations and European countries. For example, British Airways offers service to some destinations that are affiliated with the United Kingdom, and Air France and KLM focus on service to French and Dutch current or former territories.

Travel within the Caribbean

If you’re interested in island hopping around the Caribbean, options for using points and miles without going back to the U.S before flying to the next destination are pretty limited. There are some Caribbean airlines that fly directly between certain destinations, but these airlines generally aren’t available for award redemptions using currency from other airline loyalty programs.

There are a few instances where you can book inter-Caribbean award flights using points on “fifth freedom” flights operated by major airlines. British Airways offers several options including the following routes:

• Antigua (ANU) and St. Kitts (SKB) or Tobago (TAB)
• Grand Cayman (GCM) and Nassau (NAS)
• St. Lucia (UVF) and Grenada (GND) or Port of Spain (POS)

Each one-way flight can be booked for 9,750, 12,250 or 16,250 British Airways Avios for economy, premium economy or business class respectively.

Dynamic Award Pricing and Impacts

As noted above, U.S. airlines flying to the Caribbean use dynamic or variable pricing for awards. While this sometimes allows you to book awards at lower prices than the previous fixed award prices for saver awards, it also has some negative impacts.

In many cases, award prices through the operating airlines’ programs are much higher than saver award levels. Second, when there isn’t any saver award space, you usually can’t book an award through another loyalty program. This is problematic if you don’t have miles in the operating carrier’s loyalty program. It also limits your ability to book flights through partner programs that have better award pricing.

Examples are provided below for specific airlines. When feasible, we’re using similar dates and comparable routes among airlines to provide a better indication of relative award prices.

Using Travel Portals to Book Flights with Flexible Currency

With so much variation in award prices, there are situations where paying “cash” to book flights represents better value than using airline points or miles. Using flexible points, such as Chase Ultimate Rewards, to book a flight through a bank program’s travel center or portal essentially is booking a paid flight. You can earn airline miles and book flights that aren’t available for award redemption, and it sometimes costs less points or miles.

For example, if a flight costs $400 or 40,000 airline miles when booking directly with the airline, that is a 1 cent per mile redemption rate, leaving taxes and fees and points earned out of the calculation. Sometimes, you can get better value by redeeming flexible currency through a travel portal.

Chase Ultimate Rewards generally offers the best value for booking flights with points through its portal. If you have a Chase Sapphire Preferred® Card, you can book a $400 flight for 32,000 Ultimate Rewards points, at a 1.25 cents per point (cpp) redemption rate. The same flight would cost only 26,667 points for Chase Sapphire Reserve® cardholders, who can redeem points through the portal at a 1.5 cpp rate.

Bilt points can be redeemed at 1.25 cents each towards flights through the Bilt Rewards portal.

With American Express, Capital One and Citi, using flexible currency points or miles to book flights through their travel portals generally is at 1 cent each. The exception is The Business Platinum Card® from American Express (rates & fees) which gets a 35% points rebate for business and first class flights, or for flights booked with the airline you elected for your airline fee credit.

Using flexible currency, at 1 cent each or more, may make sense in some situations, such as:

• You don’t have airline program miles to book the flight.
• Airline program award prices are high compared to cash prices, and you prefer not spending cash. An example is a $200 flight where the award price is 30,000 airline miles, but the flight could be purchased with 20,000 ThankYou Points through Citi’s travel center.
• Points or miles earned and other benefits of a revenue booking are important for your situation. For example, some airline programs only allow members to earn elite credit for or upgrade paid flights.
• You want to book flights that aren’t available for an award booking.

American Airlines Flights

American Airlines Overview

American Airlines, including regional partner American Eagle, has an extensive Caribbean route network with service to about 30 destinations. Its primary U.S. airports for nonstop Caribbean flights are Charlotte (CLT) and Miami (MIA). American also operates some nonstop flights from Austin (AUS), Boston (BOS), Chicago-O’Hare (ORD), Dallas (DFW), New York (JFK and LGA), Philadelphia (PHL) and Washington-National (DCA). Connecting flights are available from other U.S. airports. Some service is seasonal, with additional flights typically being operated during peak season from mid-Dec. to mid-Apr.

American AAdvantage members can earn miles in multiple ways including: credit card welcome bonuses and spending, partners (including travel, financial, shopping, dining) and crediting flights (on American Airlines or partner airlines) to the program. Credit cards that earn AAdvantage miles include:

• AAdvantage® Aviator® Red World Elite Mastercard®
• AAdvantage® Aviator® World Elite Business Mastercard®
• American Airlines AAdvantage MileUp℠ Card
• Citi® / AAdvantage® Executive World Elite Mastercard®
• Citi® / AAdvantage® Platinum Select World Elite Mastercard
• CitiBusiness / AAdvantage Platinum Select World Mastercard

You also can obtain AAdvantage miles by transferring points from participating programs. American Airlines isn’t a transfer partner for any of the four major flexible currency programs, but Bilt Rewards and Marriott Bonvoy points can be transferred to American AAdvantage.

AAdvantage Awards

American Airlines offers three types of awards: MileSAAver, AAnytime and Web Special awards. American’s award chart shows one-way award prices between the contiguous 48 U.S. states and the Caribbean:

• MileSAAver Off Peak awards, available only on specific dates, for 12,500 miles in main cabin
• MileSAAver Peak awards for 15,000 miles in main cabin and 25,000 miles in business / first
• AAnytime Level 1 or 2 awards for 27,500 or 37,500 miles in main cabin and 50.000 or 60,000 miles in business / first

Web Special awards are variably priced, so they may require fewer, the same or more miles than MileSAAver awards. Web Special awards can’t be changed but can be canceled without fees. For cancellations, miles are reinstated, and taxes and fees paid are returned to the original form of payment.

If your travel dates are flexible, it’s easiest to search for availability on American Airlines’ website by selecting a date and navigating to the calendar view to find dates with lower award prices (overall, and you can filter to see a specific cabin and number of stops). For example, the lowest available one-way main cabin awards in a recent search from Miami (MIA) to St. Maarten (SXM) are 10,000 miles. Many dates have main cabin awards for less than the MileSAAver level.

Let’s look more closely at Jan. 10 as an example, one of the days with award availability beginning at 10,000 miles. After sorting by “Main Cabin” you can see the lowest priced flight.

For dates with main cabin award availability at 15,000 miles (the MileSAAver level) or less, there usually will be two award types available. Booking code “T” indicates MileSAAver availability, and “Y” indicates Web Special availability.

Once you click the main cabin award price box for this flight, you can select either the Web Special award for 10,000 miles or the MileSAAver award for 15,000 miles.

In contrast, on Jan. 12, the least expensive main cabin award is 21,000 miles. The details only show booking code “Y” availability.

If you want to book business / first class, applicable booking codes are “U” for MileSAAver awards and “J” for Web Special awards. If your travel dates are flexible, you can view a month of availability using the calendar view filtered to show business / first availability. For Jan. 2023, the lowest cost awards for business / first class are 38,000 miles one-way, so there won’t be any MileSAAver availability.

While the previous examples are for nonstop flights, American doesn’t charge per segment, so connecting itineraries could require the same number or fewer miles than a nonstop flight. The following main cabin award from Cleveland (CLE) to St. Martin (SXM) with a connection in MIA is the same price as the MIA to SXM nonstop flight.

American Partner Awards

There are several other airline loyalty programs that can be used to book awards on American Airlines flights. There is one big caveat: partner programs only have access to MileSAAver (booking code “T” or “U”) space. Besides the programs discussed below, it’s possible to book American Airlines flights through other partners, including Cathay Pacific, Etihad, and Japan Airlines.
Let’s look at the same examples for travel from Miami (MIA) to St. Maarten (SXM). On Jan. 10, a date with MileSAAver availability, British Airways has award availability for 11,000 Avios.

In contrast, British Airways doesn’t show any award availability on Jan. 12, when American Airlines only has Web Special availability.

The bottom line for booking partner awards is to find flights where American Airlines has booking code T (main cabin) or U (business / first) availability. If you’re considering a wide range of travel dates, starting on American Airlines’ website to find dates with MileSAAver award availability may save time.

Alaska Airlines Mileage Plan

Transfer partners: Points can only be transferred to Alaska Mileage Plan from Marriott Bonvoy.

Alaska’s awards aren’t priced dynamically, so they may offer good value on some routes where the itinerary includes U.S. connecting segments operated by Alaska or American. Alaska Mileage Plan award prices to the Caribbean can include flights from Canada and the state of Alaska, while American Airlines’ awards cover the continental U.S. only.

Alaska Mileage Plan’s one-way pricing is:

• 17,500 miles for economy
• 27,500 miles for business / first (on a two cabin plane, or for business class on a three cabin plane)
• 52,500 miles for first class on a three cabin plane

British Airways Executive Club

Transfer partners: American Express, Bilt, Capital One, Chase and Marriott points can be transferred to British Airways.

Aer Lingus, British Airways, Iberia, Qatar Airways and Vueling each have separate loyalty programs but use a common currency called Avios. The programs sometimes have different award pricing, but Avios can be transferred among programs.

British Airways Executive Club and Iberia Plus programs used to have different rules and award pricing for travel on American Airlines. The differences made British Airways more valuable for booking short nonstop one-way flights and Iberia more valuable for booking connecting flights on round-trip itineraries. In May 2021, Iberia changed its redemption rules for American Airlines awards to align with British Airways’ program.

British Airways and Iberia awards are distance-based and per segment, so the number of Avios needed depends on the origin, connecting location, and destination. For North American flights, the least expensive one-way awards for American Airlines economy flights are 7,500 Avios. Shorter flights, such as Miami (MIA) to Nassau, Bahamas (NAS) fall into this tier.

British Airways generally is the preferred Avios program for North American travel on American Airlines for two reasons. First, Iberia’s website doesn’t recognize some North American airports. For example, we couldn’t successfully search for St. Maarten (SXM) on Iberia’s website. Second, Iberia often has higher fees on American Airlines flights within North America, compared to British Airways. Award prices for the nonstop one-way American Airlines economy flight from Miami (MIA) to Nassau (NAS) shown above are 7,500 Avios in both programs, but Iberia’s fees are $30.80 compared to $5.60 for British Airways.

Many nonstop economy flights to the Caribbean from eastern U.S. airports like Charlotte (CLT) or Miami (MIA) are 11,000 Avios one-way, as shown above. Longer flights like Charlotte (CLT) to Aruba (AUA) also fall into this tier.

If you’re considering premium class awards to the Caribbean, British Airways generally charges double the number of Avios for business class, compared to economy awards. This pricing would apply to business or first class on two cabin planes, which typically are used on American Airlines’ Caribbean routes.

Using Avios can be a good use of miles for nonstop flights between the U.S. and the Caribbean, but if you need to add one or more domestic flights to connect from your home airport to the Caribbean flight, each segment adds to the award price. For example, travel from Cleveland (CLE) to Miami (MIA) to St. Maarten (SXM) is 20,000 Avios through British Airways.

Qantas Frequent Flyer

Transfer partners: American Express, Capital One, Citi and Marriott are transfer partners with Qantas.

Qantas is another Oneworld partner with a distance-based award chart that can offer good value, especially on short flights in economy. Since Qantas charges more than double the number of points for business class compared to economy, Avios redemptions generally offer better value for business class awards. Most Caribbean flights will price within the first few zones, as shown below.

Delta Airlines Flights

Delta Overview

Delta operates a fairly large Caribbean network as shown on the airline’s route map. Delta’s primary airport in the U.S. for nonstop service is Atlanta (ATL), and Delta also operates service, some seasonal, from Boston (BOS), Detroit (DTW), Minneapolis-St. Paul (MSP) and New York-Kennedy (JFK). Frequency varies by day, season and route. Delta offers connecting service from other U.S. airports.

SkyMiles members can earn miles in multiple ways including: credit card welcome bonuses and spending, partners (including travel, shopping, dining) and crediting flights (on Delta or partner airlines) to the program. Credit cards that earn SkyMiles include:

• Delta SkyMiles® Blue American Express Card (Rates & Fees)
• Delta SkyMiles® Gold American Express Card (Rates & Fees)
• Delta SkyMiles® Platinum American Express Card (Rates & Fees)
• Delta SkyMiles® Reserve American Express Card (Rates & Fees)
• Delta SkyMiles® Gold Business American Express Card (Rates & Fees)
• Delta SkyMiles® Platinum Business American Express Card (Rates & Fees)
• Delta SkyMiles® Reserve Business American Express Card (Rates & Fees)

You also can obtain SkyMiles by transferring points from participating programs: American Express Membership Rewards and Marriott Bonvoy. Transfers from Membership Rewards incur an excise tax offset fee of $0.0006 per point, up to a maximum fee of $99.

SkyMiles Awards

Delta doesn’t have an award chart, and its award pricing is fully dynamic. Delta sometimes offers flash sales that feature lower award prices between selected city pairs and travel dates. The best way to find dates with lower priced awards is to search for a specific route over a range of dates. When searching on Delta’s website, check the boxes for “Shop with miles” and “My dates are flexible” as well as entering other search criteria.

The results displayed for the selected class of service are for seven days, the selected date and three days before and after it. In this example, we’re looking for main cabin one-way flights from Atlanta (ATL) to St. Maarten (SXM) in Jan. 2023.

If your travel dates are more flexible, you can select “Price Calendar” to see a monthly calendar of lowest priced award availability. Once again, the least expensive one-way economy award is 23,000 SkyMiles.

Looking at first class award availability on the same route, the lowest priced awards are 92,500 SkyMiles one-way.

On Jan. 10, there is a nonstop flight at the lowest monthly prices for both main cabin and first-class awards. Although these award prices exceed the saver levels for one-way awards on other airlines and what Delta used to charge for saver awards when they had an award chart, the main cabin flight for 23,000 SkyMiles behaves like a saver award in that the space is available for partners to book.

To find a lower priced award for Delta first-class, we searched during peak hurricane season. The lowest priced award is 56,000 miles one-way. This award space is available for partners to book.

Delta Partner Awards

Since Delta is a member of SkyTeam and also partners with other airlines outside of SkyTeam, there are several partners that may be useful for booking awards on Delta operated flights.

Like other airlines, Delta limits partner access to award space. Unfortunately, there is no way to know, from the Delta award price or displayed codes, if a flight has award availability that partners can book. The single digit booking code – “N” for main cabin, “S” for Comfort+ and “O” for first — only identifies the cabin. While a two digit code, for example “NT” is displayed in flight details, this code isn’t indicative of partner availability.

There is a better chance that dates with lower priced awards on Delta’s website might have award availability with partners. If you have points and miles that enable you to book through Delta or partner programs, you may want to check multiple partners to find the best award prices for your specific plans.

Air France-KLM Flying Blue

Transfer partners: It’s easy to earn Flying Blue miles, since the program allows transfers from American Express, Bilt, Capital One, Chase, Citi and Marriott.

The number of Flying Blue miles required to book partner flights is “based on the booking class and flight distance,” according to the Flying Blue website. There is a miles price estimator tool available. Results for Atlanta (ATL) to St. Maarten (SXM) are:

Looking at the same dates in Jan. 2023 used for Delta and other partner airline searches, we found Flying Blue availability in economy class for Jan. 8, 9 and 10 for 19,500 miles. This is more than the “starting from” miles the estimator tool shows for the route.

Similarly, the business class award flight on Sep. 12 is available through Flying Blue for a higher price than the estimator tool’s “starting from” mileage amount.

For both the economy and business class awards above, it would be better to book through another partner that charges less miles, but given the variability of Flying Blue award prices, it’s worth checking Flying Blue.

Korean SkyPass

Transfer partners: The only program that currently allows transfers to Korean Air is Marriott Bonvoy.

Korean Air is in the SkyTeam alliance and has a region based award chart for partner awards for tickets issued through March 31, 2023. Korean’s SkyTeam Award pricing is based on round-trip travel. Korean Air defines regions differently than many airlines, with the entire United States (including Puerto Rico and the U.S. Virgin Islands) in “North America” and most other Caribbean islands in the “Central America” region.

Round-trip award prices within North America are 25,000 miles for economy class and 45,000 miles for business or first class. An itinerary from anywhere in the United States with connecting flights to St. Thomas (STT) or San Juan (SJU) booked through Korean SkyPass can provide good value compared to other programs. This is because many programs: price awards based on distance and number of segments or have a fixed award chart that includes the U.S. Virgin Islands and Puerto Rico in the same region as other Caribbean islands.

Round-trip awards between North America and Central America are 35,000 miles for economy and 75,000 miles for business or first class. The Atlanta (ATL) to St. Maarten (SXM) route would be in this category, and if booking a round-trip award, the price each way would be 17,500 miles.

Beginning Apr. 1, 2023, Korean will switch to a distance based award chart with per segment award pricing.

In general, this pending change represents a devaluation for many situations, but let’s take a look at two hypothetical itineraries where the difference between the current and future award chart varies significantly.

Example 1: Cincinnati (CVG) to Atlanta (ATL) to St. Thomas (STT) and back in first class

• Under the current chart, this can be booked for 45,000 miles round-trip.
• Under the future chart, this award would require 22,000 miles each way between Cincinnati and Atlanta and 40,000 miles each way between Atlanta and St. Thomas. That’s a total of 124,000 miles round-trip, which is almost three times the current price.

Example 2: Round-trip Atlanta (ATL) to St. Thomas (STT) in economy (a 1,701 mile one-way flight)

• Under the current chart, this could be booked for 35,000 miles round-trip.
• Under the future chart, this would require 20,000 miles each way or 40,000 miles round-trip, which is 5,000 miles more than the current price.

Virgin Atlantic Flying Club

Transfer partners: It’s easy to obtain Virgin Atlantic Flying Club miles, since Virgin Atlantic, or its parent company Virgin Red, allows transfers from American Express, Bilt, Capital One, Chase, Citi and Marriott.

Virgin Atlantic uses a distance-based award chart to determine award prices for Delta Airlines flights on routes that don’t include the United Kingdom or Europe. Award prices are per segment, so travel between the U.S. and Caribbean should fall into the shorter distance categories below. Award prices for nonstop, shorter flights in Delta’s main cabin are pretty reasonable, but award prices increase for connecting itineraries, longer distances and premium cabin flights.

We checked the same route and date range used to search on Delta’s website to compare award availability and prices.

The lowest Delta main cabin award prices between Atlanta and St. Maarten in Jan. 2023 were 23,000 SkyMiles, with availability several days at that price. Both dates with the lowest Delta pricing had Virgin Atlantic award availability, but comparing two dates that had Delta availability for 24,000 miles, only one had Virgin Atlantic availability. When available, Virgin Atlantic one-way awards are 12,500 Flying Club miles, as expected for the 1,701 mile flight. Virgin Atlantic doesn’t impose fuel surcharges on routes entirely within North America, so Virgin Atlantic taxes and fees are the same as booking through Delta.

The Delta first class award on Sep. 12, for which Delta charges 56,000 miles one-way, is available through Virgin Atlantic for 45,000 miles one-way.

JetBlue Flights

JetBlue Overview

JetBlue offers nonstop Caribbean service from Boston (BOS), Fort Lauderdale (FLL) and New York-Kennedy (JFK) to many Caribbean destinations as indicated on their route map. Connecting service is available from other U.S. cities.

What sets JetBlue apart from other airlines that fly to the Caribbean is JetBlue Mint, which is available on select Caribbean nonstop routes and dates. Mint is JetBlue’s premium class product, and the cabin always features lie-flat seats in suites with every seat having direct aisle access. JetBlue Mint food and service also is considered among the best offered on U.S.-based airlines.

TrueBlue members can earn points in multiple ways including: credit card welcome bonuses and spending, partners (including travel, shopping, dining) and crediting flights (on JetBlue or some partner airlines) to the program. Barclays issued credit cards that earn JetBlue points include:

• JetBlue Card
• JetBlue Plus Card
• JetBlue Business Card

You also can obtain TrueBlue points by transferring flexible currency from American Express, Chase and Citi.

TrueBlue Awards

JetBlue award pricing is completely dynamic and closely tied to paid fares. JetBlue offers four types of paid fares: Blue Basic, Blue, Blue Extra and Mint. Blue Basic fares can’t be booked with points, so we’re using Blue fares for main cabin examples.

In general, using TrueBlue points to book JetBlue flights in economy provides a redemption value of about 1.4 to 1.6 cents per point (cpp). Let’s look at an example for one-way nonstop travel from New York-Kennedy (JFK) to St. Maarten (SXM) in Jan. 2023.

The cash fare is $154, and the points cost is 9,400 points plus $5.60 taxes. This is approximately 1.57 cpp (calculated by subtracting taxes from the cash fare, and dividing the result by 9,400). We didn’t include two offsetting, variable factors in the calculation:

• Paid fares earn TrueBlue points, with the earning rate varying based on fare type, purchase channel, payment method and TrueBlue status.
• JetBlue Plus or JetBlue Business cardholders get a 10% rebate when booking with points.

Using TrueBlue points to book Mint cabin offers a lower redemption value compared to main cabin. For the displayed Boston (BOS) to St. Maarten (SXM) one-way nonstop Mint flight, cash prices are $1,432 and points prices are 140,000 points plus $5.60 taxes. That’s a redemption value of about 1.02 cpp.

JetBlue Partner Awards

JetBlue isn’t in any of the major airline alliances, but JetBlue has separate partnerships with several airlines, including an alliance with American Airlines. Partner programs generally aren’t useful for redeeming points on JetBlue flights to the Caribbean.

Southwest Airlines Flights

Southwest Overview

Southwest offers nonstop Caribbean service, most often from Washington-Baltimore (BWI) or Fort Lauderdale (FLL), and sometimes from other U.S. airports to several Caribbean destinations per their route map. Southwest also has connecting flights from other U.S. airports.

Unlike other carriers flying from the U.S. to the Caribbean, Southwest doesn’t have a first or business class cabin, so if you’re seeking a premium cabin flight, Southwest isn’t an option.

Rapid Rewards members can earn points in multiple ways including: credit card welcome bonuses and spending, partners (including travel, shopping, dining) and from flying on Southwest. Chase issued credit cards that earn Rapid Rewards points include:

• Southwest Rapid Rewards® Plus Credit Card
• Southwest Rapid Rewards® Premier Credit Card
• Southwest Rapid Rewards® Priority Credit Card
• Southwest® Rapid Rewards® Performance Business Credit Card
• Southwest® Rapid Rewards® Premier Business Credit Card

You also can obtain Rapid Rewards points by transferring points from Chase and Marriott.

Although Southwest revenue flights aren’t usually available on third-party travel agency websites, it’s possible to use flexible currency to book Southwest flights. You usually can’t do this through the online portals, and in most cases, the redemption value is less than using Southwest points. It still may be worth considering this option if you don’t have Rapid Rewards points or flexible currency that can be transferred to Southwest and don’t want to pay cash.

Summaries by program are:

• American Express Membership Rewards: You have to call Amex Travel to book Southwest flights with points.
• Bilt Rewards: You have to call Bilt Rewards to book Southwest flights. We confirmed this with a customer service representative, but you may have to try multiple agents to find one who can do this.
• Capital One Venture Miles: You can’t use miles to book through Capital One Travel, but if you pay with an eligible Capital One miles earning credit card, you can be reimbursed for the purchase with miles at 1 cent per point. For example, it would take 16,500 points to offset the $165 flight discussed above.
• Chase Ultimate Rewards: You can transfer points to Southwest or book through the portal. The latter option might be better for Chase Sapphire Reserve® cardholders, since the redemption value is 1.5 cents per point when booking travel through Ultimate Rewards, or 1.25 cents per point with the Chase Sapphire Preferred® Card or Ink Business Preferred® Credit Card.
• Citi ThankYou Points: You have to call the Citi Travel Center to book Southwest flights with points.

Rapid Rewards Awards

Southwest award pricing is completely dynamic and closely tied to paid fares. Southwest offers four types of fares: Business Select, Anytime, Wanna Get Away plus and Wanna Get Away. You can compare the fare types, but even the least expensive Wanna Get Away fares include two free checked bags, and cash fares are refundable for a Southwest credit that doesn’t expire. Southwest offers all four fare types whether booking with cash or Rapid Rewards points.

If your travel dates are flexible, beginning with the Low Fare calendar is helpful to find dates with the best fares. You can choose to view fares in points or cash. Let’s search for a nonstop flight from Orlando (MCO) to Aruba (AUA) in Jan. 2023

Once results are displayed, you can easily toggle between seeing cash or points fares, and use the dropdown to change the fare type.

After selecting Jan. 10, one of the dates with the lowest fare, you can view available flights and see prices for each fare type.

Changing the view to points yields the following results.

If you’re trying to decide between paying cash or using points, you can calculate the redemption value by noting the number of points earned with the cash fare, as shown above for the Wanna Get Away fare.

The calculation is:

• Numerator: Cash booking price minus cash amount for taxes and fees on points booking
• Denominator: Points required for points booking plus points earned with cash booking
  For this example, that is ($165 – $15.60) / (10,375 + 750) = $0.0134 or 1.34 cents per point.

The result is consistent with industry estimates of Southwest points being worth 1.3 or 1.4 cents each.

Southwest Partner Awards

Southwest doesn’t have any airline partners with points or miles that can be used to book flights on Southwest.

United Airlines Flights

United Overview

United flies to many Caribbean destinations, with its most extensive nonstop service from New York-Newark (EWR) and multiple nonstop flights from other United hubs including Chicago-O’Hare (ORD), Houston-Intercontinental (IAH) and Washington-Dulles (IAD). Some service is seasonal. United also offers connecting flights from other U.S. cities.

United flights to the Caribbean typically are on two cabin planes. Depending on the route, the premium cabin is referred to as business or first class. When looking at partner award charts that have three pricing tiers (economy, business and first), the business class price should apply to United’s premium cabin.

United MileagePlus members can earn miles in multiple ways including: credit card welcome bonuses and spending, partners (including travel, financial, shopping, dining) and crediting flights (on United or partner airlines) to the program. Chase issued credit cards that earn United miles include:

• United Club℠ Infinite Card
• United℠ Explorer Card
• United Gateway℠ Card
• United Quest℠ Card
• United TravelBank Card
• United℠ Business Card

You also can obtain MileagePlus miles by transferring points from Chase, Bilt and Marriott. While Marriott points transfer to most airline programs at a 3:1 ratio with a 5,000 mile bonus for every 60,000 Marriott points transferred, there is an extra 10% bonus for transferring Marriott points to United.

MileagePlus Awards

United prices awards dynamically and no longer publishes an award chart. United has two types of awards: Saver and Everyday. Saver awards generally are priced lower and are available for partner booking.

Let’s look at some examples of United awards. For Jan. 2023, we searched for flights from Washington-Dulles (IAD) to St. Thomas (STT).

The lowest price awards are 17,500 miles one-way in economy class.

Here are the results for first class awards on the same route.

Jan. 3 has the lowest award prices in both economy and first class. When viewing the details, the economy flight is designated as a Saver award, but the lowest priced first-class itinerary, which has a connection, doesn’t have this designation.

Despite searching multiple routes over many months, we didn’t see any premium class flights designated as Saver awards. The example below for 30,300 miles was the least expensive premium class award found.

United Partner Awards

United is a member of Star Alliance, which is the largest airline alliance, so there are many airline partners to consider. We’re going to focus on a subset of partners that may provide better award pricing, due to favorable award charts.

Partner awards should be available when United shows “Saver” awards when searching on United’s website without being logged into your MileagePlus account. The latter point is important, since United sometimes offers its elite members and credit card customers enhanced award availability. When searching for partner awards, you need to look for regular Saver space.

The note “Saver Award” often appears for specific flights with availability in economy class, but we didn’t find business or first-class Saver availability in our Caribbean searches. Saver space should reference booking class “X” for economy class and “I” for premium class. You can search for availability in these booking classes on ExpertFlyer.

Awards annotated, like in the example below, with “United Economy YN” or “United First JN” (also “United Business JN”) aren’t available for partner bookings.

Air Canada Aeroplan

Transfer partners: It’s relatively easy to earn Aeroplan miles, since the program allows transfers from American Express, Bilt, Capital One, Chase and Marriott.

In addition to Aeroplan being an option for booking flights on United, Air Canada also flies nonstop from some Canadian airports to some Caribbean destinations. Since it’s possible to search for and travel on a combination of United operated and Air Canada operated flights to the Caribbean, we’re looking at awards on United flights only, Air Canada flights only or a combination.

Aeroplan considers the U.S., Canada, and the Caribbean as part of its North America region.

Aeroplan has distance-based award charts for each region, but there is some variation in award pricing, particularly on Air Canada operated flights. There is a downloadable award chart and price predictor tool on Aeroplan’s website. The “Within North America” section applies to travel between the U.S., Canada and the Caribbean.

Aeroplan is expected to make some minor changes to its award pricing beginning Sep. 1, 2022, but the information released so far didn’t include any changes to “Within North America” award pricing.

Let’s look at a few examples with Aeroplan awards.

From Washington-Dulles (IAD) to St. Thomas (STT) on Jan. 3 on a 1,606 mile United Airlines nonstop flight with Saver availability in economy, Aeroplan shows award availability for 12,500 miles. The award price matches the expected pricing on Aeroplan’s distance-based award chart and is less than United’s price of 17,500 miles. Aeroplan’s fees are higher, mostly because Aeroplan charges a partner booking fee on all partner awards.

The next example shows how award pricing varies when including flights operated by Air Canada.

The first row shows a nonstop flight from Toronto-Pearson (YYZ) to Providenciales (PLS). The 1,568 mile flight is operated by Air Canada. The economy award price is within the range shown on the award chart for Air Canada operated flights, but the business class award price exceeds the range.

The second row shows a route with a connection, with one Air Canada operated segment and one United operated segment. The pricing seems to be a mix reflecting variable pricing on the Air Canada segment and fixed pricing on the United segment. Before getting excited about a relatively low priced business class award, note that only the short flight from Toronto to Newark is in business class.

Avianca LifeMiles

Transfer partners: LifeMiles are fairly easy to obtain, since they can be transferred from American Express, Capital One, Citi, and Marriott.

Avianca has region-based award pricing, and its United Airlines award chart shows one-way award prices between the U.S. and the Caribbean at 17,500 miles in economy, 30,000 miles in business class and 45,000 miles in first class.

For Jan.3, a date with United Saver availability in economy from Washington-Dulles (IAD) to St. Thomas (STT), Avianca shows award availability for 17,500 miles. Avianca charges a $25 partner booking fee (not displayed below), in addition to the taxes United charges.

Overall, it’s usually less expensive to book a United Airlines Caribbean flight through Aeroplan instead of LifeMiles, unless the one-way flight distance is more than 2,750 miles. For example, flights from Denver (DEN) to St. Thomas (STT) with a connection in Washington-Dulles (IAD) are further than 2,750 miles. This itinerary could be booked as an award flight with 22,500 Aeroplan miles or 17,500 Avianca miles.

Turkish Miles&Smiles

Transfer partners: Turkish has three options for transferring flexible currency to their program: Capital One, Citi and Marriott.

Although Turkish Airlines’ region definitions and application of its award chart are contradictory and booking through Miles&Smiles can be challenging, we’re discussing Turkish Airlines because of the potential for low priced award options on some routes.

The regions applicable to Caribbean travel are North America and South America. Turkish Airlines defines these regions to include the following countries and areas.

Turkish’s promotional award chart shows round-trip prices, which translate to the following one-way award prices:

• Within North America: 10,000 miles in economy, 15,000 miles in business, and 25,000 miles in first
• Between North and South America: 52,500 miles in economy, 75,000 miles in business and 115,000 miles in first

Miles&Smiles redemptions are good value only for awards that are considered within North America or lower prices for travel within the United States (7,500 miles for economy and 12,500 miles for business).

To search for Miles&Smiles awards on United operated flights, it’s important to use the Star Alliance search on Turkish’s website. To do this, log into your Miles&Smiles account, go to the dropdown under your name and select “Miles Transactions.” On the next page, click the link for “Book now” in the box labeled “Star Alliance award tickets.” The resulting search screen is shown below.

We found economy award availability on the Jan. 3 United economy flight from Washington-Dulles (IAD) to St. Thomas (STT) for 7,500 miles + $5.60 one-way. Turkish priced the award according to Turkish’s within the U.S. award pricing.

But, searches for Turkish awards on multiple dates from New York-Newark (EWR) to San Juan (SJU), when United economy “Saver” space was available, didn’t show any award availability through Miles&Smiles.

We also found other Caribbean destinations pricing as North America to South America awards, at 52,500 miles one-way in economy through Miles&Smiles. In this example, the United Saver award is only 12,200 miles.

There are several factors that make it complicated to find and book lower cost award flights through Miles&Smiles.

• Turkish’s regions are unclear: The North America region includes “Antilles Nether,” but countries generally considered to be part of the Netherlands Antilles are separately noted as part of Turkish’s South America region. Similarly, the United States is in the North America region, but U.S. territories, that are geographically within the Caribbean, are listed in the South America region. As shown above, some within U.S. awards don’t follow the regional award pricing at all.
• Turkish’s website doesn’t always show award availability on flights where United has Saver awards: This award space should be available for partners to book.
• Booking online through Turkish often is challenging: Even when you find award availability online, for months, it wasn’t possible to complete ticketing on the Turkish website. That issue seems to be resolved, but many people still report issues with ticketing awards.
• Calling or emailing Turkish Airlines is hit or miss: Sometimes calling or emailing one of the Turkish ticketing offices provides a way to book awards that aren’t displayed or bookable online, but success through Turkish agents varies.

Final Thoughts

When booking flights to the Caribbean using points and miles, you should consider all options:

• Redeeming airline miles through an operating carrier’s program.
• Transferring flexible currency (if needed) and redeeming miles through a partner airline’s program.
• Redeeming flexible currency through a bank’s travel center or portal.

With airlines pricing awards dynamically and limiting partners’ ability to book award seats, redeeming the operating airline’s own miles can be extremely useful. One example is for flights to the Caribbean in premium cabins, where there often is no award availability for partner bookings. Another time when using the operating carrier’s miles is advantageous is when the operating carrier’s awards cost less miles than partner awards or have lower fees, including change and cancellation fees.

On the other hand, especially if you’re mostly interested in booking economy awards to the Caribbean, there are specific partners and routes that offer better redemption value when redeeming miles though partners compared to redeeming miles through the operating carrier’s program. Flexible currency also is valuable to allow you to pick which program is the best option for booking a particular flight.