The Caribbean is one of the world’s most affordable destinations, especially when you consider the tropical wonders that await.
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The natural wonders, cultural excursions, and laidback lifestyle call to Americans year after year. That being said, not all Caribbean islands fit into the affordable category. The smaller the island, the pricier hotels and flights are. Toss in other considerations, like tourist infrastructure and figuring out if English is spoken, and planning a trip to the Caribbean can quickly get complex.
Looking for a little shortcut, especially when it comes to savings? While most islands offer a range of lodgings, from ultra-lux to budget-friendly, you should be focused first on which islands you can fly to without overspending. That plane ticket could easily eat away at your travel funds if you aren’t mindful about where you go.
After all, even Caribbean islands located side by side might have wildly different air travel costs based on which airlines serve them and the state of their airport(s).
Here’s what you need to know about finding the cheapest Caribbean destinations to fly to. The islands are listed in order of affordability.
Flight pricing was pulled from the Google Travel Explore page from Houston, Miami, Atlanta, Los Angeles, & New York City for a one-week trip in the next six months.
Cheapest Caribbean destinations to fly to from the US
Puerto Rico
Flying into: San Juan, Puerto Rico
Want a tropical destination that doesn’t require a passport? Head to Puerto Rico. You can spend a few days in the historic capital of San Juan, then take off to explore small islands like Vieques, rainforests like El Yunque, and beaches filled with bioluminescence.
Find a hotel or a private rental in Puerto Rico.
Curacao
Flying into: Willemstad
Enjoy endless beach days on pristine shores in Curacao. Explore sites like Sheta Boka National Park for their natural wonders, home to rare orchids and tropical wildlife, then take on cultural adventures in the capital of Willemstad—a UNESCO World Heritage Listed site.
Find a hotel or a private rental in Curacao.
Aruba
Flying into: Oranjestad
Aruba has a dry climate that differentiates it from other Caribbean islands. It’s been dubbed ‘One Happy Island’ thanks to its 300-odd days of pure sunshine a year. Just know that in lieu of tropical, lush forests, you can expect rugged, desert-like landscapes.
Find a hotel or a private rental in Aruba.
Bahamas
Flying into: Nassau
You’re likely already familiar with the Bahamas, including the popular main hub of New Providence Island and smaller outposts like Alice Town. As such, you might not need reminding: the Bahamas is one of the cheapest Caribbean destinations to fly to from the US.
Find a hotel or a private rental in the Bahamas.
St. Thomas (US Virgin Islands)
Flying into: Charlotte Amalie
Like Puerto Rico, the US Virgin Islands let you explore the tropics without a passport. The USVI is home to three islands, including St Croix, St John, and St Thomas. The latter is one of the cheapest Caribbean destinations to fly to from the US, thanks to its popular airport, located near the capital of Charlotte Amalie. Expect wide, mile-long sand beaches, lush forests laced with hiking trails, and historic sites like Blackbeard’s Castle, which dates back to the 1600s.
Find a hotel or a private rental in St. Thomas.
Dominican Republic
Flying into: Punta Cana
Punta Cana has quickly become one of the Caribbean’s most sought-after destinations. The laidback lifestyle adds to the charm of its sprawling, palm-tree-dotted beaches and its wide range of affordable resorts and hotels. Expect water adventures like dolphin-spotting, snorkeling, and even deep-sea fishing excursions.
Find a hotel or a private rental in the Dominican Republic.
Jamaica
Flying into: Montego Bay or Negril
Jamaica is currently recovering from widespread hurricane destruction, meaning not all resorts and hotels are up and running. However, trips to Montego Bay and Negril are usually known for their emerald mountains and colorful, pristine beaches. You can hike the mountains and valleys, discover gorgeous waterfalls, and even explore pirate ruins in places like Port Royal.
Find a hotel or a private rental in Jamaica.
Grand Cayman (Cayman Islands)
Flying into: George Town
This British overseas territory might perk up ears since it’s often mentioned as a tax haven. But Grand Cayman is also a tropical paradise. Lodging isn’t the cheapest, but flights are affordable and accessible year-round. You can stick to Seven Mile Beach, check out the famous Stingray City sandbars, and explore historic sites like Pedro St. James Castle, which was built back in 1780.
Find a hotel or a private rental in Grand Cayman.
Anguilla
Flying into: The Valley
Anguilla is a small island that’s known for its sleepy, soft-sand beaches, along with its crystalline waters. Resorts can be found around the island, many with fine dining restaurants and other upscale amenities. Uniquely, Anguilla (which is also a British overseas territory) has a Heritage Trail that lets you dive deep into the island’s history, including a preserved plantation house from the 1700s.
Find a hotel or a private rental in Anguilla.
St. Kitts & Nevis
Flying into: Basseterre
Welcome to the smallest nation-state in the Western Hemisphere. St. Kitts & Nevis is composed of two small islands—St. Kitts, where the capital of Basseterre is located, and Nevis. Similar to Anguilla, the island has gone to great lengths to preserve its history, which you can learn about it at the Brimstone Hill Fortress National Park. Aside from its stunning tropical beaches, St. Kitts & Nevis is also a haven for wildlife thanks to its expansive rainforests.
