[Expired] [Deal Alert] Last-Minute Caribbean Holiday Deals From $152 Round-Trip

Updated: June 8, 2026, 5:49am CDT

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Table of Contents

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

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Update:

The offer mentioned below has expired and is no longer available.

If you’re looking for some cheap, last-minute deals for the winter holiday season — or want to avoid a cold snap in the northern half of the country — look no further.

There are incredible deals from the continental U.S. to the famously sunny and warm Caribbean starting at around $150 round-trip. Additionally, no passport is required for certain destinations.

Let’s check out these fantastic deals.

Fare Deal — Details

We’re seeing flight deals across the Caribbean, from Puerto Rico and the U.S. Virgin Islands to Aruba and the Bahamas, starting at well under $200 round-trip.

Some of the cheapest deals include flights to San Juan (SJU) in Puerto Rico and St. Thomas (STT) in the U.S. Virgin Islands. However, there are some fantastic deals to Nassau (NAS), Aruba (AUA), Providenciales, Turks and Caicos (PLS), and many other islands. Even better — some of these deals are available during the winter holidays, which means you can spend Christmas or the New Year in paradise!

If you’re interested in these flights, you can explore dates on Google Flights and book directly with your preferred airline.

Class: Economy
Routes: Atlanta (ATL), Boston (BOS), New York (JFK), Newark (EWR), and Miami (MIA) to select Caribbean destinations
Dates: December 2025 through January 2026
Rates: As low as $152 round-trip in economy

Frontier MIA SJU — Image Credit: Google Flights

Hot Tip:

Note that most of these deals are in their respective airline’s basic economy. Basic economy tickets come with little more than a personal bag and a seat on the plane. If you want more flexibility during your trip, you can pay a higher fare for a standard economy ticket, which includes checked bags and allows you to choose your seat.

How To Book and Where To Stay

Most of these routes have pretty good availability between December 2025 and January 2026, so you shouldn’t have trouble finding dates that work for you.

Make sure to book your flight using a card that rewards you for travel purchases. Some of our favorites include the Platinum Card^® from American Express, Chase Sapphire Reserve^®, and the Capital One Venture X Rewards Credit Card.

Hyatt Regency Grand Reserve Puerto Rico grounds — Hyatt Regency Grand Reserve Puerto Rico. Image Credit: Katie Seemann

Of course, getting to the Caribbean is only half the battle. Once you’re there, you’ll need a place to stay. Here are a few of our recommendations:

Puerto Rico: Hyatt Regency Grand Reserve Puerto Rico (from 20,000 World of Hyatt points per night)
Puerto Rico: Hilton Ponce Golf & Casino Resort (from 50,000 Hilton Honors points per night)
U.S. Virgin Islands: The Ritz-Carlton, St. Thomas (from 82,000 Marriott Bonvoy points per night)
Aruba: Holiday Inn Resort Aruba-Beach Resort & Casino (from 52,000 IHG One Rewards points per night)

Final Thoughts

There are some pretty solid deals (albeit in basic economy) to the Caribbean for travel this winter and spring. We’re even seeing some affordable points options for hotels, including at some ultra-luxe resorts.

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