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Simpson Bay

$84+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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Cheap 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 December 5, 2025.

This JetBlue deal was found by Cheapflights users on 12/4. 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.
Thu 12/187:30 amBOS - SXM
Nonstop4h 14mJetBlue
Tue 12/231:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Deal found 12/4$339
This American Airlines deal was found by Cheapflights users on 12/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:59 amBOS - SXM
1 stop6h 27mAmerican Airlines
Thu 1/84:24 pmSXM - BOS
1 stop8h 27mAmerican Airlines
Deal found 12/3$341
This Super.com deal was found by Cheapflights users on 12/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:45 amBOS - SXM
1 stop7h 30mSpirit Airlines
Fri 12/123:20 pmSXM - BOS
1 stop9h 36mSpirit Airlines
Deal found 12/4$342
This Delta deal was found by Cheapflights users on 12/4. 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.
Thu 12/189:15 pmBOS - SXM
1 stop16h 35mDelta
Wed 12/244:15 pmSXM - BOS
1 stop18h 02mDelta
Deal found 12/4$343
This Delta deal was found by Cheapflights users on 12/4. 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.
Wed 12/175:40 amBOS - SXM
1 stop7h 48mDelta
Thu 12/251:45 pmSXM - BOS
1 stop11h 09mDelta
Deal found 12/4$345
This Priceline deal was found by Cheapflights users on 12/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:30 amBOS - SXM
Nonstop4h 14mMultiple Airlines
Wed 12/243:20 pmSXM - BOS
1 stop9h 37mMultiple Airlines
Deal found 12/4$348
This Delta deal was found by Cheapflights users on 12/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:40 amBOS - SXM
1 stop7h 48mDelta
Sat 12/274:15 pmSXM - BOS
1 stop17h 05mDelta
Deal found 12/3$349
This American Airlines deal was found by Cheapflights users on 12/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:40 pmBOS - SXM
2 stops18h 45mAmerican Airlines
Fri 12/195:33 pmSXM - BOS
2 stops15h 29mAmerican Airlines
Deal found 12/3$350
This American Airlines deal was found by Cheapflights users on 12/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:36 pmBOS - SXM
2 stops18h 44mAmerican Airlines
Sat 12/201:15 pmSXM - BOS
1 stop10h 32mAmerican Airlines
Deal found 12/3$354
This Priceline deal was found by Cheapflights users on 12/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:30 amBOS - SXM
Nonstop4h 14mMultiple Airlines
Thu 12/253:40 pmSXM - BOS
1 stop18h 52mMultiple Airlines
Deal found 12/4$355
This American Airlines deal was found by Cheapflights users on 12/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:24 pmBOS - SXM
1 stop22h 35mAmerican Airlines
Wed 12/243:28 pmSXM - BOS
1 stop9h 05mAmerican Airlines
Deal found 12/3$357
This Priceline deal was found by Cheapflights users on 12/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:45 amBOS - SXM
1 stop7h 30mMultiple Airlines
Tue 12/165:00 pmSXM - BOS
1 stop20h 12mMultiple Airlines
Deal found 12/3$358

Find 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 December 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$272
(Trip.com)

One-way from

$84
(United Airlines)

Popular in

July

Cheapest in

September

Average price

$1,026
Provider with most accurate pricing for Portland-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-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. 18% potential increase in price ($168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 5, 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

Wed 4/15

6:00 am-2:07 pm

1 stop8h 07m

Simpson Bay Princess Juliana

Wed 4/22

3:15 pm-11:36 pm

1 stop8h 21m

$272

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 1/17

5:09 pm-3:22 pm

2 stops21h 13m

Simpson Bay Princess Juliana

Sat 1/24

5:01 pm-12:05 pm

2 stops20h 04m

$323

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 2/1

8:50 pm-12:30 pm

1 stop14h 40m

Simpson Bay Princess Juliana

Tue 2/10

4:20 pm-7:33 am

1 stop16h 13m

$345

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 2/3

5:35 am-2:55 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Tue 2/10

4:20 pm-8:27 am

1 stop17h 07m

$345

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 2/2

8:00 pm-12:30 pm

1 stop15h 30m

Simpson Bay Princess Juliana

Tue 2/10

4:20 pm-7:33 am

1 stop16h 13m

$345

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 1/28

5:35 am-2:55 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Fri 1/30

4:20 pm-9:17 am

1 stop17h 57m

$345

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 2/3

5:35 am-2:55 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Wed 2/4

4:20 pm-7:24 am

1 stop16h 04m

$345

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/25

8:10 am-3:51 pm

1 stop6h 41m

Simpson Bay Princess Juliana

Thu 1/29

2:52 pm-9:52 pm

1 stop8h 00m

$347

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 1/26

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sun 2/1

4:55 pm-11:49 pm

1 stop7h 54m

$347

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 1/28

5:35 am-2:55 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Sat 1/31

4:20 pm-9:14 am

1 stop17h 54m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 37 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 8h 07m. 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Maine to Simpson Bay

Discover the top 3 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 December 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$794FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$540Average$631FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$566Average$707FlexibilityNo cancel feeOn-time71%

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