Simpson Bay

$93+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SXM
Dec 3 — Dec 101
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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 November 3, 2025.

Round-trip from

$277
(Expedia)

One-way from

$93
(Cheapflightsfares)

Popular in

March

Cheapest in

October

Average price

$657
From Connecticut to Simpson Bay Princess Juliana
One-way flight from Connecticut to Simpson Bay Princess Juliana
Highest demand for flights based on searches. 11% potential increase in price ($84 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in November 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 November 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Mon 11/176:38 amEWR - SXM
1 stop6h 37mSpirit Airlines
Fri 11/213:20 pmSXM - EWR
1 stop10h 11mSpirit Airlines
Deal found 11/3$268
This Travelocity deal was found by Cheapflights users on 11/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:46 amEWR - SXM
1 stop7h 29mMultiple Airlines
Sun 12/1411:30 amSXM - EWR
1 stop12h 00mMultiple Airlines
Deal found 11/1$277
This Expedia deal was found by Cheapflights users on 11/2. 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.
Sat 11/226:20 amEWR - SXM
1 stop6h 55mMultiple Airlines
Thu 11/2711:30 amSXM - EWR
1 stop12h 00mMultiple Airlines
Deal found 11/2$278
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Wed 12/105:46 amEWR - SXM
1 stop7h 29mMultiple Airlines
Sun 1/1811:30 amSXM - EWR
1 stop12h 00mMultiple Airlines
Deal found 11/1$289
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Mon 11/176:38 amEWR - SXM
1 stop6h 37mSpirit Airlines
Sat 11/223:20 pmSXM - EWR
1 stop10h 11mSpirit Airlines
Deal found 11/2$291
This Expedia deal was found by Cheapflights users on 11/2. 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 12/105:46 amEWR - SXM
1 stop7h 29mSpirit Airlines
Sat 12/133:20 pmSXM - EWR
1 stop9h 32mSpirit Airlines
Deal found 11/2$294
This Flysmarter deal was found by Cheapflights users on 11/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1711:30 amJFK - SXM
Nonstop4h 08mJetBlue
Wed 11/264:19 pmSXM - JFK
Nonstop4h 29mJetBlue
Deal found 11/2$294
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 11/216:20 amEWR - SXM
1 stop6h 55mMultiple Airlines
Thu 11/2711:30 amSXM - EWR
1 stop12h 00mMultiple Airlines
Deal found 11/2$295
This Flysmarter deal was found by Cheapflights users on 11/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1411:35 amJFK - SXM
Nonstop4h 08mJetBlue
Tue 12/232:10 pmSXM - JFK
Nonstop4h 34mJetBlue
Deal found 11/2$297
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/65:46 amEWR - SXM
1 stop7h 29mSpirit Airlines
Wed 12/103:20 pmSXM - EWR
1 stop9h 32mSpirit Airlines
Deal found 11/2$300
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/136:00 amLGA - SXM
1 stop7h 15mSpirit Airlines
Sat 12/203:20 pmSXM - LGA
1 stop8h 11mSpirit Airlines
Deal found 11/2$301
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 12/1011:35 amJFK - SXM
Nonstop4h 08mJetBlue
Sun 12/283:45 pmSXM - JFK
Nonstop4h 34mJetBlue
Deal found 11/2$301

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 November 3, 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

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Sun 11/23

11:21 am-4:29 pm

Nonstop4h 08m

Simpson Bay Princess Juliana

Thu 11/27

4:15 pm-7:44 pm

Nonstop4h 29m

$303

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Sun 1/25

7:30 am-12:30 pm

Nonstop4h 00m

Simpson Bay Princess Juliana

Fri 1/30

4:20 pm-8:07 pm

Nonstop4h 47m

$303

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Fri 1/2

8:03 am-1:11 pm

Nonstop4h 08m

Simpson Bay Princess Juliana

Fri 1/9

5:36 pm-9:10 pm

Nonstop4h 34m

$303

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Wed 1/7

9:15 am-2:28 pm

Nonstop4h 13m

Simpson Bay Princess Juliana

Wed 1/14

3:43 pm-7:17 pm

Nonstop4h 34m

$303

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Fri 11/28

11:21 am-4:29 pm

Nonstop4h 08m

Simpson Bay Princess Juliana

Sat 12/6

6:08 pm-9:29 pm

Nonstop4h 21m

$303

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 12/17

6:00 am-2:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Wed 12/24

1:45 pm-11:36 pm

1 stop10h 51m

$311

ProvidenceSimpson Bay

PVD - SXM

PVDSXM

Providence-TFGreen

Tue 12/16

6:34 pm-4:25 pm

2 stops20h 51m

Simpson Bay Princess Juliana

Tue 12/23

1:39 pm-9:12 am

2 stops20h 33m

$316

NewarkSimpson Bay

EWR - SXM

EWRSXM

Newark

Mon 1/19

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Thu 1/22

1:55 pm-12:55 am

1 stop12h 00m

$317

New YorkSimpson Bay

JFK - SXM

JFKSXM

New York John F Kennedy Intl

Wed 1/21

7:30 am-12:30 pm

Nonstop4h 00m

Simpson Bay Princess Juliana

Wed 2/11

4:20 pm-8:07 pm

Nonstop4h 47m

$319

New YorkSimpson Bay

LGA - SXM

LGASXM

New York LaGuardia

Tue 1/20

6:59 am-4:28 pm

1 stop8h 29m

Simpson Bay Princess Juliana

Tue 1/27

5:33 pm-7:53 am

2 stops15h 20m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
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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, October is the cheapest month in which you can book a flight from Connecticut to Simpson Bay (average of $383). Flying from Connecticut to Simpson Bay in August is currently the most expensive (average of $586). 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 4h. JetBlue provides one of the quickest options available for as low as $303. 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 Spirit Airlines, with whom users have recently found tickets for as low as $94. However, be on the lookout for offers from American Airlines and Delta, 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, October is the cheapest month in which you can book a flight from Connecticut to Simpson Bay (average of $383). Flying from Connecticut to Simpson Bay in August is currently the most expensive (average of $586). 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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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$425Average$573FlexibilityNo cancel feeOn-time62%
DeltaCheapest$529Average$657FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$529Average$705FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$626Average$785FlexibilityNo cancel feeOn-time69%

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