[Deal Alert] Last-Minute Caribbean Holiday Deals From $274 Round-Trip

Updated: December 23, 2024, 12:13pm CST

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Fare Deal — Details
How To Book and Where To Stay
Final Thoughts

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If you’re looking for some cheap, last-minute deals — or want to avoid an East Coast cold snap — look no further. There are incredible deals to the warm Caribbean region starting at under $300 round-trip. Even better: you can bring in the New Year in a new country!

Let’s check out these holiday deals.

Fare Deal — Details

Make no mistake: cheap flight deals are still available, even for last-minute holiday travel.

We’re seeing flight deals to several Caribbean countries on airlines like American Airlines, Delta Air Lines, Frontier Airlines, and United Airlines. Some of the cheapest deals include flights to Aruba (AUA) and St. Thomas (STT) in the U.S. Virgin Islands.

If you’re interested in any of these flights, play around with dates on Google Flights and book directly with your respective airline.

Class: Economy
Routes: Atlanta (ATL), Boston (BOS), Baltimore (BWI), Charlotte (CLT), and Chicago (ORD) to Aruba (AUA), Grand Cayman (GCM), Montego Bay (MBJ), Punta Cana (PUJ), and St. Thomas (STT)
Dates: Late December 2024 through early January 2025
Rates: As low as $274 round-trip in basic economy

BOS to STT for $274 round-trip — Image Credit: Google Flights

Hot Tip:

Note that the cheapest deals are in basic economy, which limits the number of bags you can bring on board and charges a fee for seat selection. If you want to upgrade your ticket to the less-restrictive standard economy (at least on the Big 3 airlines), you’ll pay at least $50 more.

How To Book and Where To Stay

There’s pretty good availability between the end of December and the first half of January on most of these routes. Several booking options will let you spend New Year’s Eve and New Year’s Day abroad.

After you’ve picked dates, make sure to book your flight using a credit card that rewards you for travel purchases. Some of our favorites include cards like The Platinum Card^® from American Express, Chase Sapphire Reserve^®, and the Capital One Venture X Rewards Credit Card.

You can fly on Southwest Airlines to Aruba to stay at Renaissance Wind Creek Aruba Resort. Image Credit: Marriott

Of course, getting to the Caribbean is only half the battle. Once you’re there, you’ll need a place to stay. There are fewer hotel deals in the region this close to the holidays, but there are still some solid options if you’re using points. Here are a few:

Aruba: Renaissance Wind Creek Aruba Resort (from 76,000 Marriott Bonvoy points per night)
Cayman Islands: Holiday Inn Resort Grand Cayman (from 50,000 IHG One Rewards points per night)
Dominican Republic: Secrets Cap Cana Resort & Spa (from 35,000 World of Hyatt points per night)
Jamaica: S Hotel Montego Bay, an SLH Hotel (from 100,000 Hilton Honors points per night)
Puerto Rico: Hyatt Regency Grand Reserve Puerto Rico (from 20,000 World of Hyatt points per night)

Final Thoughts

If you had given up on traveling during the holiday season, you’re in luck. There are some pretty solid deals (albeit in basic economy) to the Caribbean for late 2024 and early 2025 travel. We’re even seeing some affordable points options for hotels, including all-inclusive resorts.

If you’re interested in a last-minute holiday vacation, be sure to book these cheap deals before they’re gone for good!

The information regarding the Capital One Venture X Rewards Credit Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

For rates and fees of The Platinum Card^® from American Express, click here.