Cheap flights To Caribbean Islands (SXM)

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Caribbean Islands Flight Information

Traveling To
Caribbean Islands
Destination Airport IATA Code
SXM
Number of Airlines Serving
Airlines
Flight Price
Earliest Departing Flight
Latest Departing Flight

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Caribbean Islands economy flight packages

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
3.5-star property

Princess Heights Luxury Boutique Condo Hotel

Nov 17 - Nov 22

5 night stay

Boston (BOS) to Philipsburg (SXM)

United • Non-stop roundtrip • Coach
Price was $897, price is now $618 per person
$618
per person
found 1 day ago
The Villas at Simpson Bay Resort
4.0-star property

The Villas at Simpson Bay Resort

Nov 17 - Nov 22

5 night stay

Boston (BOS) to Philipsburg (SXM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,357, price is now $761 per person
$761
per person
found 1 day ago
Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

Nov 1 - Nov 6

5 night stay

Boston (BOS) to Philipsburg (SXM)

Spirit Airlines • Non-stop • Coach

Philipsburg (SXM) to Boston (BOS)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,161, price is now $708 per person
$708
per person
found 1 day ago
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Caribbean Islands first class flight packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (1,345 reviews)

Oct 27 - Nov 3

7 night stay

Boston (BOS) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,972, price is now $1,320 per person
$1,320
per person
found 14 hours ago
I had an excellent time, everything was perfect. Staff were polite and very helpful. 5 star experience.

Reviewed on Jul 31, 2025

The Villas at Simpson Bay Resort
4.0-star property

The Villas at Simpson Bay Resort

9.2/10 Wonderful! (1,241 reviews)

Oct 27 - Nov 3

7 night stay

Boston (BOS) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,346, price is now $1,543 per person
$1,543
per person
found 14 hours ago
Had a great time! Room clean and updated. Great staff and location!!

Reviewed on Aug 4, 2025

Holland House Beach Hotel
4.0-star property

Holland House Beach Hotel

9.2/10 Wonderful! (1,004 reviews)

Oct 27 - Nov 3

7 night stay

Boston (BOS) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,686, price is now $1,940 per person
$1,940
per person
found 14 hours ago
The staff are amazing and it is super convenient to stores. Breakfast was great!

Reviewed on Sep 5, 2025

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Caribbean Islands

Snag some “suite” deals when you add cheap hotel rooms to Caribbean Islands flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Caribbean Islands.

Fun for All

While shopping Orbitz sales on Caribbean Islands flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Caribbean Islands flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Caribbean Islands. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

Frequently asked questions

Which airlines fly to Caribbean Islands?
Check out the deals from the airlines that offer services to Caribbean Islands. Whether you're eager to sip Champagne in the pointy end of the plane or save dollars in economy, there'll be a seat for you. Touch down at Las Americas Intl. Airport (SDQ) with one of these reputable carriers:

  • JetBlue - 144 flights to Caribbean Islands per month
  • American Airlines - 70 flights to Caribbean Islands per month
  • Copa Airlines - 54 flights to Caribbean Islands per month

How much is a flight to Caribbean Islands?
Travelers from far and wide snapped up round-trip bargains ranging from to this week. Kicking off your journey from ()? The lowest one-way tickets were .
How to book the cheapest flight to Caribbean Islands?
Picking up cheap flights to Caribbean Islands is as simple as booking with Orbitz. But if you want to make sure you're nabbing the best flight deals around, here are a few tips to keep your wallet happy:

  • Taking off from or arriving at other airports can be more cost-effective. Enter your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below the form fields to explore your options.
  • If your travel plans aren't cast in stone, click on the 'Show flexible dates' option to view the flight deals for different departure dates. Go with any suitable cheaper fare that pops up.
  • To optimize your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
  • The early bird catches the most impressive deals, so book your tickets the moment you know your travel dates. The most affordable airfares sell like hotcakes and prices normally rise as the departure date gets closer.
  • Bundle your hotels, flights and car rental into a value-for-money package deal. Save your hard-earned dollars for things that really excite you, like exploring every corner of Caribbean Islands.
  • If you can, don't travel in peak seasons. Airfares significantly increase during school breaks, summer and other vacation periods like Easter and Thanksgiving.

What is the best time to book a flight to Caribbean Islands?
Generally speaking, January is the best month to purchase your plane ticket. This is followed by February and August. Keep this in mind while searching for a cheap flight to Caribbean Islands.
What day of the week is the cheapest to book a flight to Caribbean Islands?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Caribbean Islands. If you're after the best airfares, search across those days and you could score a terrific flight deal.
What is the cheapest day of the week to fly to Caribbean Islands?
If you're chasing cheap flights to Caribbean Islands, depart early in the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your bank account a favor.
What is the cheapest month to fly to Caribbean Islands?
Consider flying in August if you're on a tight budget. Orbitz data shows that this is generally the best month for cheap flights to Caribbean Islands. June is when airfares really go up.
Which airlines allow free cancellation?
Orbitz makes it a piece of cake to find airlines offering fare flexibility. Simply select "Filter by flexible change policies" when searching for your flights and bingo! We'll show you options that include free cancellation within 24 hours of booking, no change fees and of course, the best price.
What do I need for the flight to Caribbean Islands?
Whether you're accustomed to flying or it's your first time on a plane, it's always great to be prepared when you travel. Here are several tips and things to take into consideration:

  • Travel paperwork such as visas and some identification will be required. To avoid any unwanted delays when checking in, make certain your booking is under the exact name, gender and birth date as listed on your current ID.
  • A well-stocked carry-on bag is a must for any lengthy flight. With a few hours or more up your sleeve, you'll want something to keep you entertained on your trip. We suggest a good book (or trashy magazine), and something to snack on.
  • Both air conditioning and high altitudes can produce a cool environment. No matter what the weather is in Caribbean Islands, carry a sweater with you to keep warm on your plane trip.

How do I get cheap first-class/business deals to Caribbean Islands?
If you think a first or business-class fare is out of your price range, you may want to think again. Here are just a few tips to help you book a premium flight to Caribbean Islands for less:

  • Flexibility is everything. By being open to a range of travel dates, you'll have better odds of finding a deal on your airfares.
  • Find a low-cost airline that offers business-class seats. They usually come with more legroom and a glass of Champagne — and a more affordable price.
  • Bid for an upgrade in online auctions or upgrade your fare through your loyalty program.

What is the best time to go to Caribbean Islands?
People come from all over the map to visit Caribbean Islands in February, March and April. So if you'd love to explore this exciting destination during the popular months, this is the best time to go. As with most places in the Northern Hemisphere, summer begins June 20 in Caribbean Islands, with average daily temperatures between 80 ºF and 85 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.