Simpson Bay

$110+ Cheap flights from Connecticut to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SXM
Oct 16 — Oct 231
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Connecticut to Simpson Bay

Keep the following information in mind while searching for Connecticut to Simpson Bay flight deals. Data was last updated September 16, 2025.

Round-trip from

$290
(CheapOair)

One-way from

$110
(Expedia)

Popular in

February

Cheapest in

October

Average price

$603
From Connecticut to Simpson Bay Princess Juliana
One-way flight from Connecticut to Simpson Bay Princess Juliana
Highest demand for flights based on searches. 10% potential increase in price ($81 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in September 2025

Find flight deals from Connecticut to Simpson Bay

Cheapest flights from Connecticut to Simpson Bay
Explore the most affordable flight options available from Connecticut to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:10 amEWR - SXM
1 stop7h 50mSpirit Airlines
Sat 10/43:05 pmSXM - EWR
1 stop17h 55mSpirit Airlines
Deal found 9/14$290
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2912:00 pmEWR - SXM
1 stop7h 52mArajet
Wed 11/58:57 pmSXM - EWR
1 stop13h 33mArajet
Deal found 9/14$293
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2812:00 pmEWR - SXM
1 stop7h 30mArajet
Sun 10/128:35 pmSXM - EWR
1 stop13h 55mArajet
Deal found 9/14$297
This Arajet deal was found by Cheapflights users on 9/15. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:00 amEWR - SXM
1 stop7h 52mArajet
Thu 12/1112:25 pmSXM - EWR
1 stop11h 05mArajet
Deal found 9/15$301
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2611:00 amEWR - SXM
1 stop7h 52mArajet
Wed 12/38:57 pmSXM - EWR
1 stop13h 33mArajet
Deal found 9/15$303
This FlightHub deal was found by Cheapflights users on 9/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:00 amEWR - SXM
1 stop7h 52mArajet
Wed 11/268:57 pmSXM - EWR
1 stop13h 33mArajet
Deal found 9/14$304
This Arajet deal was found by Cheapflights users on 9/15. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/512:00 pmEWR - SXM
1 stop7h 30mArajet
Sun 10/128:35 pmSXM - EWR
1 stop13h 55mArajet
Deal found 9/15$305
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2912:00 pmEWR - SXM
1 stop7h 52mMultiple Airlines
Sat 11/13:05 pmSXM - EWR
1 stop8h 24mMultiple Airlines
Deal found 9/14$306
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/512:00 pmEWR - SXM
1 stop7h 30mMultiple Airlines
Sat 10/113:05 pmSXM - EWR
1 stop8h 24mMultiple Airlines
Deal found 9/15$311
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:25 amEWR - SXM
1 stop27h 15mMultiple Airlines
Wed 12/108:57 pmSXM - EWR
1 stop13h 33mMultiple Airlines
Deal found 9/16$313
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2611:30 amJFK - SXM
Nonstop4h 08mJetBlue
Sat 11/12:43 pmSXM - JFK
Nonstop4h 26mJetBlue
Deal found 9/15$321
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:00 amLGA - SXM
1 stop8h 00mSpirit Airlines
Sat 10/183:05 pmSXM - LGA
1 stop8h 20mSpirit Airlines
Deal found 9/15$322

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut 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 September 16, 2025.
Use the filters below to find and compare flights from Connecticut to Simpson Bay that are best for you.

Fly from

Connecticut

Fly to

Simpson Bay

Route

Depart

Return

Price

NewarkSimpson Bay

EWR - SXM

EWRSXM

Newark

Sun 9/28

12:00 pm-7:30 pm

1 stop7h 30m

Simpson Bay Princess Juliana

Sun 10/5

8:35 pm-10:30 am

1 stop13h 55m

$305

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Mon 10/27

9:20 am-1:19 pm

Nonstop3h 59m

Simpson Bay Princess Juliana

Sat 11/1

4:49 pm-9:15 pm

Nonstop4h 26m

$321

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Sun 10/26

9:20 am-1:19 pm

Nonstop3h 59m

Simpson Bay Princess Juliana

Fri 10/31

2:34 pm-7:00 pm

Nonstop4h 26m

$321

New YorkSimpson Bay

LGA - SXM

LGASXM

New York LaGuardia

Wed 11/19

6:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Wed 11/26

5:24 pm-7:42 am

2 stops15h 18m

$338

New YorkSimpson Bay

LGA - SXM

LGASXM

New York LaGuardia

Wed 11/12

6:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Tue 11/18

5:24 pm-8:07 am

2 stops15h 43m

$338

New YorkSimpson Bay

LGA - SXM

LGASXM

New York LaGuardia

Sun 11/9

6:15 am-3:57 pm

1 stop8h 42m

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-6:07 pm

1 stop28h 07m

$342

New YorkSimpson Bay

LGA - SXM

LGASXM

New York LaGuardia

Sat 10/25

10:20 am-2:57 pm

1 stop28h 37m

Simpson Bay Princess Juliana

Sun 11/2

3:00 pm-9:07 am

1 stop19h 07m

$342

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Fri 12/12

11:30 am-4:38 pm

Nonstop4h 08m

Simpson Bay Princess Juliana

Sat 12/20

5:25 pm-8:59 pm

Nonstop4h 34m

$342

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Mon 12/15

11:30 am-4:38 pm

Nonstop4h 08m

Simpson Bay Princess Juliana

Mon 12/22

2:28 pm-6:02 pm

Nonstop4h 34m

$342

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Sat 11/29

10:05 am-3:09 pm

Nonstop4h 04m

Simpson Bay Princess Juliana

Sat 12/20

5:25 pm-8:59 pm

Nonstop4h 34m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Connecticut to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Connecticut 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 Connecticut to Simpson Bay

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

Currently, September is the cheapest month in which you can book a flight from Connecticut to Simpson Bay (average of $459). Flying from Connecticut to Simpson Bay in March is currently the most expensive (average of $652). 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 Connecticut to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Simpson Bay from Connecticut?

    For a flight from Connecticut to Simpson Bay, you will be flying into Princess Juliana. Simpson Bay Princess Juliana (SXM) is just 0.5 mi from the center of the city.

  • How long is the flight from Connecticut to Simpson Bay?

    A quick flight from Connecticut to Simpson Bay can take about 3h 59m. Arajet provides one of the quickest options available for as low as $321. Airlines will cover a distance of 1684 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Connecticut to Simpson Bay one-way?

    The cheapest airline one-way is Arajet, with whom users have recently found tickets for as low as $110. However, be on the lookout for offers from Spirit Airlines and JetBlue, as they are both options that can get you from Connecticut to Simpson Bay for a low price.

  • What are the most popular routes from Connecticut to Simpson Bay?

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Connecticut 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 Connecticut to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Connecticut to Simpson Bay (average of $459). Flying from Connecticut to Simpson Bay in March is currently the most expensive (average of $652). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Connecticut to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Connecticut to Simpson Bay

Discover the top 4 airlines that operate flights from Connecticut to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$425Average$627FlexibilityNo cancel feeOn-time62%
DeltaCheapest$474Average$657FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$484Average$703FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$619Average$740FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.