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Islands Under $100? Your Best Bets for a Tropical Winter Getaway

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We hate to be the bearer of bad news, but winter is on the horizon. But the best way to usher in the changing of the seasons might just be to book your tropical getaway from the cold.

And trust us: planning ahead for a tropical winter or spring getaway pays off. We've been finding some crazy cheap fares for this winter, with flight prices as low as $96 roundtrip to islands like St. Croix in the U.S. Virgin Islands, Puerto Rico, and far beyond.

From Mexico to the Dominican Republic to the U.S. Virgin Islands and even Hawaii, many islands and countries are open to travelers. When it comes to cheap flights and accessible entry requirements, there are a handful of destinations that stand out.


Tips for Booking Your Winter Vacation

Before you start searching, there are a few things you need to keep in mind.

  1. Book on an airline with flexible change and cancellation policies. Most U.S. airlines are offering fee-free changes or cancellations on all Main Cabin fares. Take advantage of this flexibility to protect your flight's worth.
  2. Know the travel testing requirements for your destination. Do your research and check if the country you're heading to requires a negative COVID-19 test to enter. Check our country-by-country guide.
  3. Plan to get your required COVID-19 test to return back to the U.S. Yes, if flying internationally, you'll need to show proof of a negative COVID-19 test before your return flight home.
  4. Start with a cheap flight deal and build your trip out from there: follow the Flight First Rule! The flight is often the most expensive part of any trip, so let the cheap flight guide your tropical destination choice –  and trip dates.

When it comes to cheap flights, we've got you covered. Our Thrifty Traveler Premium members have been getting tons of great flight deal alerts to tropical getaways recently.

We'll give you a taste…


No Passport? No Problem!

If you'd rather stay within the U.S. but are still craving a tropical getaway, you've still got some great options. Head to Puerto Rico, the U.S. Virgin Islands, or the Hawaiian Islands, and leave your passport at home. Plus, you won't need to provide a negative COVID-19 test before returning home, since these are technically domestic flights.


Puerto Rico

If you've never been, Puerto Rico should be on your list for potential tropical getaways this year! Vaccinated Americans are welcome with no arrival testing required. Unvaccinated Americans need a negative COVID-19 test result within 72 hours of travel. No testing is required on your return flight home.

And with the flight pricing trends we've been seeing over the past few months, it's easier than ever to snag a cheap flight to Puerto Rico. Here’s a recent deal we found and sent to Thrifty Traveler Premium members under $100…roundtrip!

premium deal tropical 

Thrifty Tip: Check out our guide to San Juan to start planning your trip.


St. Croix & St. Thomas, U.S. Virgin Islands

The U.S. Virgin Islands reopened for tourism last fall. To get in, you'll need a negative COVID-19 test result taken no more than five days before travel. No return test is required to fly back to the mainland U.S.

Need a cheap flight to get you there? Lucky for you, there's been quite a few sub-$200 flights to the USVI lately! We sent this deal from several cities to Premium members recently with fares under $100 roundtrip:

premium deal tropical 

Thrifty Tip: Check out these must-dos in St. Croix while you're there.


Dreaming of the island experience without leaving the ‘U.S.'? Like the U.S. Virgin Islands, we're seeing unprecedented price drops to the Hawaiian islands. Typically, you'd pay $700 or more for a flight to the U.S.'s most exotic destination. But as of late, we've seen flights drop under $365 roundtrip to all four major islands:

premium deal tropical 

Live on the West Coast, or willing to get there on a cheap flight? You'll get even cheaper fares to Hawaii. Lately, we've seen prices from West Coast cities to Hawaii under $180 roundtrip!

premium deal tropical 

Hawaii has loosened its entry requirements: Travelers with proof of vaccination can bypass Hawaii testing and quarantine requirements. Unvaccinated travelers must still provide a negative test to enter Hawaii. Be sure to read our Master Guide to Hawaii Travel Requirements for the full low-down.


Other Tropical Destinations Open for Travel

There are plenty of islands and destinations abroad that are open to U.S. travelers if you're looking for an even bigger getaway. Just remember, you'll need a negative COVID-19 test to return from your trip abroad back to the U.S.

These are your best bets for a cheap – and easy – getaway this year.

The Dominican Republic

If you're looking for one of the easiest tropical international destinations, look no further. There are no COVID-19 testing requirements for entry to the Dominican Republic, though authorities will administer random quick breath tests to some arriving passengers.

Plus, tourists visiting a hotel can get a cheap insurance policy that will cover emergencies, COVID-19 testinglodging for prolonged stays, and the cost of changing flights in the event of an infection. This insurance can be purchased for $34 total.

Read what our first-hand account of what it's like in the Dominican Republic, or watch for yourself:


And the recent flight prices to the Dominican Republic have made the decision to go even easier. We sent Premium members this recent flight deal from just $234 roundtrip:

premium deal tropical 

Cancún, Cabo & More Mexican Beaches

Mexico is always a great choice for a cheap tropical getaway, and this year is no different. With no testing required for entry and most hotels and resorts offering COVID-19 testing for your return flight home, Mexico is an easy international option.

While there are many top cities to visit, flights to Cancun (CUN) have consistently been the lowest these past few months, dropping as low as $159 roundtrip from some cities:

premium deal tropical 

Tropical beach under $200? Say no more!

We love Cancún, but the flight deals don't stop there. We've been seeing sub-$200 flights to Puerto Vallarta, Cabo, and other Mexican beach hotspots!

premium deal tropical 

Many cheap fares like this one are already gone! Get Thrifty Traveler Premium to get cheap flights delivered straight to your inbox.



While Belize is technically coastal Central America, it is often thought of as the Caribbean because of its history and tropical coast. If you've been to several Caribbean destinations, branch out and explore up-and-coming Belize!

Lately, we've been seeing flight prices to Costa Rica and Belize drop under $300 roundtrip – over half of the usual price! In some cases, we've seen flights to Belize City drop as low as $200 roundtrip from nearly every U.S. airport:

premium deal tropicalpremium deal tropical 

Heading to Belize? You'll need a negative COVID-19 test taken within 96 hours prior to travel or testing on arrival ($50) regardless of your vaccination status.



No, flights to Jamaica don't have to break the bank. These flight prices are gone now, but we alerted Thrifty Traveler Premium members to sub-$300 flights to Jamaica a few weeks ago!

premium deal tropical 

Thrifty Tip: Use Chase or Hyatt points to book your stay at the Hyatt Ziva or Zilara all-inclusive resorts in Jamaica for free.

Start planning your island getaway! A negative COVID-19 test taken within 72 hours prior to departure is required to visit Jamaica.


Bottom Line

Whether you're looking for a winter getaway or planning ahead for Spring Break 2022, there are plenty of flight deals to get to a beach for cheap. Beat the airfare rush and start planning your winter vacation now while flights are cheap with instant alerts of price drops from your home airport.

Wondering about other destinations not on this list? Check out our country-by-country guide to see up-to-date information on travel requirements.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

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