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Simpson Bay

$604+ Cheap flights from New Haven (HVN) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from New Haven to Simpson Bay

Cheapest flights from New Haven to Simpson Bay
Explore the most affordable flight options available from New Haven to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:59 pm
HVN
-
SXM
2 stops18h 09m
Multiple Airlines
Fri 3/202:14 pm
SXM
-
HVN
3 stops31h 10m
Multiple Airlines
Deal found 1/27$604

Find flight deals from New Haven to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from New Haven (HVN) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$604
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$443
Provider with most accurate pricing for Tweed-New Haven-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Tweed-New Haven-Simpson Bay Princess Juliana flights.
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From Tweed-New Haven to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from New Haven to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from New Haven to Simpson Bay that are best for you.

Fly from

New Haven

Fly to

Simpson Bay

Route

Depart

Return

Price

New HavenSimpson Bay

HVN - SXM

HVNSXM

Tweed-New Haven

Fri 3/13

6:59 pm-1:08 pm

2 stops18h 09m

Simpson Bay Princess Juliana

Fri 3/20

2:14 pm-9:24 pm

3 stops31h 10m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Compare providers for flights from New Haven to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from New Haven to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Haven-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Haven-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Haven-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Haven-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Haven-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from New Haven to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from New Haven with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Haven to Simpson Bay

What is the cheapest month to book a flight from New Haven to Simpson Bay?

Currently, November is the cheapest month in which you can book a flight from New Haven to Simpson Bay (average of $121). Flying from New Haven to Simpson Bay in September is currently the most expensive (average of $316). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from New Haven to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on New Haven to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Haven to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Simpson Bay.

  • Can I find deals for business class flights from New Haven to Simpson Bay?

    Yes. Cheapflights offers flight deals from New Haven to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Haven to Simpson Bay?

    Currently, November is the cheapest month in which you can book a flight from New Haven to Simpson Bay (average of $121). Flying from New Haven to Simpson Bay in September is currently the most expensive (average of $316). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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