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Simpson Bay

$114+ Cheap flights from Maine 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find flight deals from Maine to Simpson Bay

Cheapest flights from Maine to Simpson Bay
Explore the most affordable flight options available from Maine to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:36 amBOS - SXM
1 stop7h 43mAmerican Airlines
Tue 11/255:24 pmSXM - BOS
1 stop8h 27mAmerican Airlines
Deal found 10/20$309
This Delta deal was found by Cheapflights users on 10/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:35 amPWM - SXM
1 stop6h 30mDelta
Sat 11/224:30 pmSXM - PWM
1 stop8h 24mDelta
Deal found 10/18$311
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:15 pmBOS - SXM
2 stops19h 04mAmerican Airlines
Wed 11/125:24 pmSXM - BOS
2 stops17h 05mAmerican Airlines
Deal found 10/18$314
This American Airlines deal was found by Cheapflights users on 10/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:15 pmBOS - SXM
1 stop18h 45mAmerican Airlines
Sat 11/225:05 pmSXM - BOS
1 stop17h 51mAmerican Airlines
Deal found 10/17$316
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:19 pmBOS - SXM
2 stops17h 17mAmerican Airlines
Sun 12/215:33 pmSXM - BOS
2 stops17h 39mAmerican Airlines
Deal found 10/18$319
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 11/156:16 amBOS - SXM
1 stop6h 59mSpirit Airlines
Sat 11/223:20 pmSXM - BOS
1 stop9h 33mSpirit Airlines
Deal found 10/19$344
This United Airlines deal was found by Cheapflights users on 10/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:26 pmBOS - SXM
1 stop21h 31mUnited Airlines
Sat 11/82:40 pmSXM - BOS
1 stop19h 50mUnited Airlines
Deal found 10/18$359
This CheapOair deal was found by Cheapflights users on 10/19. 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.
Sat 12/65:50 amBOS - SXM
1 stop7h 20mSpirit Airlines
Sat 12/133:15 pmSXM - BOS
1 stop9h 42mSpirit Airlines
Deal found 10/19$361
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/185:40 amBOS - SXM
1 stop8h 15mDelta
Tue 11/254:20 pmSXM - BOS
1 stop10h 06mDelta
Deal found 10/20$363
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:16 pmBOS - SXM
1 stop17h 03mAmerican Airlines
Tue 12/25:24 pmSXM - BOS
2 stops18h 10mAmerican Airlines
Deal found 10/19$364
This United Airlines deal was found by Cheapflights users on 10/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amBOS - SXM
1 stop6h 50mUnited Airlines
Sat 12/65:00 pmSXM - BOS
2 stops18h 49mUnited Airlines
Deal found 10/18$367
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amBOS - SXM
1 stop8h 57mUnited Airlines
Sat 12/202:40 pmSXM - BOS
1 stop11h 05mUnited Airlines
Deal found 10/19$372

Cheap flight deals from Maine to Simpson Bay

Keep the following information in mind while searching for Maine to Simpson Bay flight deals. Data was last updated October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$114
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$553
Provider with most accurate pricing for Boston Logan Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Maine to Simpson Bay Princess Juliana
Search Deals
One-way flight from Maine to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 October 20, 2025.
Use the filters below to find and compare flights from Maine to Simpson Bay that are best for you.

Fly from

Maine

Fly to

Simpson Bay

Route

Depart

Return

Price

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 11/15

6:35 am-2:05 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Sat 11/22

4:30 pm-11:54 pm

1 stop8h 24m

$311

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 1/22

5:08 pm-2:31 pm

2 stops20h 23m

Simpson Bay Princess Juliana

Fri 1/30

5:33 pm-12:06 pm

2 stops19h 33m

$316

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/17

8:45 pm-12:30 pm

1 stop14h 45m

Simpson Bay Princess Juliana

Sat 1/24

5:16 pm-12:59 am

1 stop8h 43m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 2/7

8:45 pm-12:30 pm

1 stop14h 45m

Simpson Bay Princess Juliana

Sat 2/14

5:16 pm-12:59 am

1 stop8h 43m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 2/22

8:30 pm-2:56 pm

1 stop17h 26m

Simpson Bay Princess Juliana

Thu 3/5

4:26 pm-7:24 am

1 stop15h 58m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 1/26

8:30 pm-2:56 pm

1 stop17h 26m

Simpson Bay Princess Juliana

Wed 2/4

4:26 pm-7:25 am

1 stop15h 59m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 2/2

8:30 pm-2:56 pm

1 stop17h 26m

Simpson Bay Princess Juliana

Tue 2/10

4:26 pm-7:25 am

1 stop15h 59m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/9

8:30 pm-1:53 pm

1 stop17h 23m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-7:24 am

1 stop15h 39m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 11/18

5:40 am-2:55 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Tue 11/25

4:20 pm-1:26 am

1 stop10h 06m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 12/2

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-10:49 am

2 stops18h 49m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 33 results
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Best time to book a flight from Maine to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Maine 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 Maine to Simpson Bay
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Maine 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 Maine?

    For a flight from Maine 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 Maine to Simpson Bay?

    Departing from Maine to Simpson Bay will take you 6h 30m. Airlines will cover a distance of 1817 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maine 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.

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 Maine to Simpson Bay

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Top 2 airlines flying from Maine to Simpson Bay

Discover the top 2 airlines that operate flights from Maine 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$286Average$794FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$540Average$633FlexibilityNo cancel feeOn-time69%

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