[Award Alert] Wide-Open Availability on Flights to the Caribbean This Winter From 4.5K Miles

It may be the heat of the summer, but now’s the time you should start planning those trips that are 6 to 8 months out. And where else would you rather be in the middle of the winter than in the Caribbean sun?

Our team has found tons of award availability on flights from the U.S. to various destinations in the Caribbean — such as Antigua, Barbados, and the Dominican Republic. Here’s what you should know before you book.

Award Deal — Details

American Airlines is having a rare award sale, discounting the price of many flights across its expansive network. In fact, the current promotion lasts until Tuesday, July 2.

Oftentimes, you can take advantage of even cheaper deals from booking the same exact flights with Alaska Airlines Mileage Plan instead. After all, Alaska is a partner of American, and both are member airlines in the Oneworld alliance.

• Class: Economy and business
• Airline: American Airlines
• Cost: 4,500 points to 12,000 points (economy) and 9,000 to 20,000 points (business class)
• Travel Dates: December through March 2025
• Award Seats: Up to 9 passengers per route

These are our favorite kind of award alerts to find since there’s plenty of availability to bring multiple passengers.

How To Book

The best possible deal you will find is booking via Alaska Airlines Mileage Plan. These flights are operated by partner American Airlines on a route between Miami (MIA) and Montego Bay, Jamaica (MBJ). You can expect to redeem 4,500 miles in economy and 9,000 miles in business class.

For Caribbean flights that are a bit longer in distance, Alaska is charging just 7,500 miles for flights between Miami (MIA) and Bonaire (BON), Curaçao (CUR), San Juan (SJU), Anguilla (AXA), and St. Thomas (STT).

Now here’s where the real secret is. If you have a Bilt Rewards account, the program has a lucrative Rent Day promotion with an up to 50% transfer bonus to Alaska Mileage Plan on Monday, July 1. That means those same flights above can be booked for as little as 2,250 miles and 3,750 miles, respectively!

Don’t have Alaska miles or a Bilt Rewards account? You can also book many of these same flights through American Airlines AAdvantage for only slightly more — around 8,000 miles.

Final Thoughts

These can get quite pricey during high season — but booking flights to the Caribbean with points and miles can help you save a great deal of cash. You only have a few days left to take advantage of this award sale, so be sure to jump on it before it’s too late.