Deals galore: 20 popular routes to the Caribbean available for under $100 in late 2020

Apr 1, 2020

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We are all currently sticking as close to home as possible due to COVID-19, but there’s nothing wrong with dreaming of a time when travel will again open up and we can all visit the places we are currently dreaming of from our couches. While no one knows exactly when it will be safe for some to embark on leisure travel, it’s fun to dream, plan and potentially even book tickets with flexible change and cancelation rules.

From where I sit, some crystal clear water, white sand and tropical drinks sounds like a pretty darn perfect post-quarantine vacation. With that in mind, here is a sampling of one-way paid and award flight deals we are seeing for the second half of 2020 to the Caribbean.

Visit TPG’s guide to all coronavirus news and updates

Park Hyatt St. Kitts (Photo by Zach Griff/The Points Guy)
Park Hyatt St. Kitts (Photo by Zach Griff/The Points Guy)

Editors note: Don’t book travel unless you fully understand the penalties around changing or canceling if the COVID-19 still situation warrants such measures in the second half of the year. TPG does not recommend leisure travel at this juncture, but we are crossing our fingers and toes for travel later in 2020.

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Flight deals currently available to the Caribbean

Atlanta – San Juan: $56

Deals to the Caribbean for under $100 each way from Atlanta are a bit harder to find than from many other U.S. cities, but if you are OK with a low-cost carrier like Frontier, there are many dates available for $56 to San Juan until mid-November.

Related: A beginner’s guide to visiting Puerto Rico

Boston – St. Martin: $90

One-stop flights to St. Martin are available on American, Delta and United into mid-November. These are basic economy fares; expect full economy fares to start $15 to $35 higher each way.

Related: St. Marin’s inexpensive must-see attractions for families

Chicago – Nassau: $86

Nonstop flights on United are available on Saturdays into mid-November in basic economy for $86 each way, with regular economy costing $30 more each way.

Related: How to visit Atlantis on a budget

Chicago – Aruba: $96

United has $96 nonstop flights on a couple of Saturdays in late-October and early-November in basic economy. Regular economy will cost $30 more.

Chicago – Providenciales: $86

Nonstop flights on United are available on a couple of Saturdays in late-October and early-November in basic economy for $86 each way, with regular economy costing $30 more each way.

Related: Best credit cards for booking airfare

Dallas – Port of Spain: $90

One-stop flights to Trinidad and Tobago on United are available for $90 on most days into mid-November. Regular economy flights will cost $30 more per direction.

Houston – Grand Cayman: $86

You can find nonstop flights at this price on United Airlines into mid-November. These are basic economy fares; expect full economy fares to start $30 higher each way.

Houston – Bonaire: $86

You can find nonstop flights at this price on United Airlines into mid-November. These are basic economy fares; expect full economy fares to start $30 higher each way.

Houston – St. Martin: $90

One-stop flights to St. Martin are available on Delta and United into mid-November. These are basic economy fares; expect full economy fares to start $30 higher each way.

Houston – Grand Cayman: $86

Nonstop flights at this price on United Airlines are available into mid-November. These are basic economy fares; expect full economy fares to start $30 higher each way.

Related: Beachfront luxury with IHG points — A review of the Kimpton Seafire Grand Cayman

Kansas City – Aruba: $100

One-stop flights on United or Delta are available into mid-November to Aruba. These are basic economy fares; expect full economy fares to start $15 to $35 higher each way.

Los Angeles – Nassau: $90

There are one-stop flights on both Delta and United available on a large variety of dates into mid-November. These are basic economy fares; expect full economy fares to start around $30 higher each way.

Los Angeles – Grand Cayman: $90

There are one-stop flights on Delta and United available on a large variety of dates into mid-November. These are basic economy fares; expect full economy fares to start $15 to $40 higher each way.

Los Angeles – St. Martin: $90

There are one-stop flights on American, Delta and United available on a large variety of dates into mid-November. These are basic economy fares; expect full economy fares to start $15 to $35 higher each way.

Miami – Bridgetown, Barbados: $85

Nonstop flights to Barbados are available until late-October in basic economy on a variety of dates on American at this price. Expect full economy seats to be $15 more in each direction of travel.

Related: How to vacation on Barbados on miles and points

Phoenix – Grand Cayman: $90

There are one-stop flights on American, Delta and United into Grand Cayman available on a large variety of dates into mid-November. These are basic economy fares; expect full economy fares to start $15 to $35 higher each way.

New York – San Juan: $73

Nonstop flights on United to San Juan are available in basic economy on United from $73 each way into mid-November. Expect full economy fares to be $30 higher each way. You can pay even less if you fly an ultra low-cost carrier such as Spirit or Frontier.

New York – Aruba: $86

Nonstop flights on United to Aruba are available in basic economy from $86 each way into late-October. Expect full economy fares to be $25 higher each way.

New York – Providenciales (Turks and Caicos): $86

Nonstop flights on United to Providenciales are available in basic economy from $86 each way into mid-November. Expect full economy fares to be $30 higher each way.

Related: Turks and Caicos Airport Observation Desk is a planespotter’s paradise

San Francisco – Aruba: $100

One-stop flights on United and Delta are available in basic economy for $100 each way into mid-November. Expect full economy fares to be $30 to $35 higher each way.

(Photo of Aruba by Zach Honig/The Points Guy)

Need more Caribbean inspiration? Check out TPG’s hub of trip-planning resources for trips to the islands.

Mileage deals to the Caribbean

While mileage flight prices to the Caribbean are lower than normal into mid-November 2020, the deals to the Caribbean using miles aren’t as good as those with cash at the moment. However, there are always exceptions to every general rule. For example, we’re seeing New York – Nassau from 5,500 Delta SkyMiles or Los Angeles – Aruba from 12,000 Delta SkyMiles. Using United miles you can take lots of Caribbean routes from about 13,000 miles each way.

If you’re sitting on American Airlines miles, there are lots of award travel deals on with AAdvantage to the Caribbean for 10,000 miles each direction. Use the American Airlines award map tool to quickly spot the best deals on miles.

Related: Tips for finding cheap award flights

How to find your own flight deals

The above is just a sampling of what we’re seeing to the Caribbean, and it’s highly likely the routes you are most interested in aren’t on this list. That’s not a problem if you know how to search for your own flight deals, and here are some of our favorite tools for doing so.

Explore with Google Flights

Start exploring at Google Flights. You can search flights to your dream destinations from multiple airports to help you spot the best deal. Or, you can search from your destination (“Where from?” field) to any gateway in the United States by typing “USA” in the “Where to?” field. You’ll get a map showing the cheapest flights to airports around the country.

Here’s a map of prices for New York City to the Caribbean from Google Flights.

Related: How to be an advanced user of Google Flights

Decide if you’ll pay with cash or points

When you find an airfare deal, you’ll need to decide if the deal is best on cash or points. That’s a personal decision that only you can make (and conserving cash right now isn’t a bad plan). However, some would say that these prices are so low that it would be a shame to “waste” miles or points unless the award deals are correspondingly low at or below the recommend TPG valuation numbers. We found that the frequent flyer programs that are the most dynamically priced are currently the ones with some of the best award prices, though that’s more true for domestic flights than those to the Caribbean at the moment.

Related: Should you use miles or cash to buy airline tickets?

Understand cancellation policies before buying an airline ticket

Finally, before buying any airline ticket in the current realities, understand the cancellation and rebooking policies for the carrier you book. Airlines have been adjusting their policies to be more friendly for future bookings, but what that means can vary from airline to airline, and they may differ depending on whether you used cash or miles. While you’re now often able to rebook an airline ticket for a future date without a change fee, just remember that you’ll likely still be on the hook for any fare difference from your old ticket to the new one.

Related: Airline coronavirus change and cancellation policies

If you’re booking an airline ticket with points or miles, here are the best ways to avoid change and cancellation fees on award tickets. You can also factor in using a credit card with good built-in travel insurance (though that doesn’t kick in simply because you choose not to travel.)

Saint Thomas
(Photo by John Duarte/Getty Images)

Bottom line

No one can guarantee when we’ll be able to travel, especially internationally. The coronavirus situation is fluid with no firm end date in sight — yet. If you’re willing to make some speculative bookings for the second half of this year, you could end up traveling and having a fantastic time — or you might need to cancel or rebook for 2021. Go into each reservation with your eyes open and a firm understanding of the cancellation/rebooking terms.

Let us know in the comments below if you decide to book something for late this year or early 2021.

Additional reporting by Andrea M. Rotondo

Featured image of Grace Bay, courtesy of Shutterstock

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