Cheap Flight Deals to Simpson Bay from CA $144
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How to find cheap flights to Simpson Bay?
The cheapest prices found with in the last 7 days for return flights were CA $333 and CA $144 for one-way flights to Simpson Bay for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| YYZ | Simpson Bay | November 14 to November 21 | CA $333 |
| YUL | Simpson Bay | December 10 to December 17 | CA $397 |
| JFK | Simpson Bay | October 5 to October 8 | CA $401 |
| JFK | Simpson Bay | October 5 to October 8 | CA $401 |
| EWR | Simpson Bay | December 9 to December 14 | CA $415 |
| BOS | Simpson Bay | October 28 to October 31 | CA $496 |
| PHL | Simpson Bay | November 27 to December 1 | CA $510 |
| MIA | Simpson Bay | October 5 to October 7 | CA $516 |
| FLL | Simpson Bay | October 28 to November 3 | CA $549 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| YYZ | Simpson Bay | September 20 to September 27 | CA $396 |
| YUL | Simpson Bay | September 18 to September 19 | CA $468 |
| BOS | Simpson Bay | September 19 to September 22 | CA $991 |
| EWR | Simpson Bay | September 18 to September 20 | CA $1,111 |
| EWR | Simpson Bay | September 18 to September 20 | CA $1,111 |
Your guide to flights to Simpson Bay,
JetBlue Airways, Air Transat fly to Simpson Bay, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Simpson Bay currently costs between CA $333 and CA $1,111. Prices vary, but for the best fares, travel in October when prices are at their lowest.
Top tips for finding cheap flights to Simpson Bay
The cheapest flight for a round trip to Simpson Bay is currently CA $333. When you search for flights to Simpson Bay, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Simpson Bay for nearby days. The cheapest month to travel to Simpson Bay is November from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Simpson Bay
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Simpson Bay with Travelocity
We have top deals on plane tickets even for last minute flights to Simpson Bay, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Simpson Bay for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Simpson Bay
Hilton Vacation Club Flamingo Beach St. Maarten
"Didn't expect that the Hotel was so well up to date. a lot of activities and very easy to stay"
Reviewed on Sep 13, 2026
Simpson Bay Resort, Marina & Spa
"This resort has it all great pools and restaurants plus the suites and villas all have kitchens and most have balconies with a view. Plus the beach area which is shared with the Hilton is private and beautiful with awesome views of the Caribbean. At night it is very safe to walk around the large ..."
Reviewed on Sep 13, 2026
Hilton Vacation Club Royal Palm St. Maarten
Travel Inn Hotel
"This property was great for the 3 nights we spent. Location was prefect, supermarket, restaurants were all in walking distance. The balcony is very small, plus the ac unit was out there, so it made sitting out side a little difficult. WiFi was very choppy. There is free parking. The price was great, ..."
Reviewed on Aug 27, 2026
Luxury Hotels in Simpson Bay
Villa Bianca
Mary's Boon Beach Resort & Spa
"Simply very good place"
Reviewed on Sep 12, 2026
The Atrium Beach Resort and Spa, an Ascend Collection Resort
"."
Reviewed on Sep 12, 2026
Simpson Bay Resort, Marina & Spa
"This resort has it all great pools and restaurants plus the suites and villas all have kitchens and most have balconies with a view. Plus the beach area which is shared with the Hilton is private and beautiful with awesome views of the Caribbean. At night it is very safe to walk around the large ..."
Reviewed on Sep 13, 2026
Family Friendly Hotels in Simpson Bay
Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay Resort, Marina & Spa
"This resort has it all great pools and restaurants plus the suites and villas all have kitchens and most have balconies with a view. Plus the beach area which is shared with the Hilton is private and beautiful with awesome views of the Caribbean. At night it is very safe to walk around the large ..."
Reviewed on Sep 13, 2026
The Villas at Simpson Bay Resort
"Every thing was great"
Reviewed on Sep 13, 2026
Hilton Vacation Club Flamingo Beach St. Maarten
"Didn't expect that the Hotel was so well up to date. a lot of activities and very easy to stay"
Reviewed on Sep 13, 2026
Best Simpson Bay Flight and Hotel Packages
Simpson Bay flight + hotel packages - economy flights
Simpson Bay flight + hotel packages - first class flights
Need a car after flight to Simpson Bay?
Economy
Compact
Midsize
SUV
Frequently asked questions
Plane Tickets To Simpson Bay
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Simpson Bay. Browse through our inventory to explore a wide range of cheap flights to Simpson Bay to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Simpson Bay as you anxiously await to exit the plane and explore what Simpson Bay has to offer. Considering all the amazing local food and culture in Simpson Bay, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Simpson Bay to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Simpson Bay without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Simpson Bay with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Simpson Bay today!
Need more than a Flight to Simpson Bay?
Explore More Ways to Travel with Travelocity
- All Inclusive Resorts & in Sint Maarten
- Cheap Hotels in Sint Maarten
- Sint Maarten Hotels
- Lower Prince's Quarter Hotels
- Hotels near Maho Beach
- Maho Reef Hotels
- Guest Houses in Philipsburg
- All Inclusive Resorts & in Philipsburg
- Philipsburg Hotels
- Villas in Philipsburg
- Hotels near Princess Juliana Intl.
- Apartments in Sint Maarten
- B&B in Sint Maarten
- Condos in Sint Maarten
- Extended Stay Hotels in Sint Maarten
- Guest Houses in Sint Maarten
- Hostels in Sint Maarten
- Houseboat Rentals in Sint Maarten
- Resorts in Sint Maarten
- Villas in Sint Maarten
- Tamarind Hill Estates Hotels
- Flights to Philipsburg
- Flights to Sint Maarten
- Delta Toronto (YYZ) to Philipsburg (SXM) flights
- Westjet Toronto (YYZ) to Philipsburg (SXM) flights
- Westjet Montreal (YUL) to Philipsburg (SXM) flights
- Flights from Toronto to Philipsburg
- Flights from Paris to Philipsburg
- Flights from Rome to Philipsburg
- Flights from Detroit (DTW) to Philipsburg (SXM)
- Flights from Basseterre (SKB) to Philipsburg (SXM)
- Flights from Vancouver (YVR) to Philipsburg (SXM)
- Flights from Toronto (YYZ) to Philipsburg (SXM)
- Ace Rental Cars in Philipsburg
- Car rental Philipsburg
- Convertible Car Rentals in Sint Maarten
- Car rental Sint Maarten
- Economy Car Rentals in Philipsburg
- Economy Car Rentals in Sint Maarten
- Firefly Rental Cars in Philipsburg
- Full-Size Car Rentals in Sint Maarten
- Luxury Car Rentals in Sint Maarten
- Mini Car Rentals in Sint Maarten
- Payless Rental Cars in Princess Juliana Intl.
- Payless Rental Cars in Simpson Bay
- Rent A Wreck Rental Cars in Philipsburg
- Standard Car Rentals in Sint Maarten
- Suv Car Rentals in Sint Maarten
- Van Car Rentals in Sint Maarten