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Simpson Bay

$276+ Cheap flights from Portland, ME (PWM) 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap flight deals from Portland to Simpson Bay

Cheapest flights from Portland to Simpson Bay
Explore the most affordable flight options available from Portland to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.

This Vliegwinkel deal was found by Cheapflights users on 2/10. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:00 am
PWM
-
SXM
1 stop9h 20m
JetBlue
Wed 4/153:11 pm
SXM
-
PWM
1 stop8h 48m
JetBlue
Deal found 2/10$276
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/65:07 pm
PWM
-
SXM
2 stops18h 31m
American Airlines
Wed 4/152:24 pm
SXM
-
PWM
2 stops19h 30m
American Airlines
Deal found 2/10$351
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/285:57 pm
PWM
-
SXM
2 stops19h 19m
American Airlines
Fri 3/61:29 pm
SXM
-
PWM
2 stops22h 11m
American Airlines
Deal found 2/10$406
This United Airlines deal was found by Cheapflights users on 2/9. 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 2/285:45 am
PWM
-
SXM
1 stop9h 12m
United Airlines
Fri 3/62:52 pm
SXM
-
PWM
1 stop8h 26m
United Airlines
Deal found 2/9$416
This KAYAK deal was found by Cheapflights users on 2/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
PWM
-
SXM
1 stop7h 42m
JetBlue
Wed 7/1511:10 am
SXM
-
PWM
1 stop12h 47m
JetBlue
Deal found 2/10$457
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Sun 3/85:40 pm
PWM
-
SXM
2 stops19h 36m
American Airlines
Sun 3/154:01 pm
SXM
-
PWM
1 stop20h 13m
American Airlines
Deal found 2/8$487

Find flight deals from Portland to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Vliegwinkel)

Popular in

July

Cheapest in

September

Average price

$658
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 Portland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($182 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 February 11, 2026.
Use the filters below to find and compare flights from Portland to Simpson Bay that are best for you.

Fly from

Portland

Fly to

Simpson Bay

Route

Depart

Return

Price

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 4/6

6:00 am-3:20 pm

1 stop9h 20m

Simpson Bay Princess Juliana

Wed 4/15

3:11 pm-11:59 pm

1 stop8h 48m

$276

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 4/6

5:07 pm-11:38 am

2 stops18h 31m

Simpson Bay Princess Juliana

Wed 4/15

2:24 pm-9:54 am

2 stops19h 30m

$351

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 2/28

5:57 pm-2:16 pm

2 stops19h 19m

Simpson Bay Princess Juliana

Fri 3/6

1:29 pm-10:40 am

2 stops22h 11m

$406

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 2/28

5:45 am-3:57 pm

1 stop9h 12m

Simpson Bay Princess Juliana

Fri 3/6

2:52 pm-10:18 pm

1 stop8h 26m

$416

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 3/28

6:49 pm-1:16 pm

2 stops18h 27m

$305

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 8/8

6:50 pm-3:09 pm

2 stops20h 19m

$310

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 8/8

9:52 am-11:20 am

3 stops25h 28m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Compare providers for flights from Portland 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 Portland to Simpson Bay in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
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 Portland, Maine-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-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 Portland, Maine-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 Portland to Simpson Bay

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

What is the cheapest month to book a flight from Portland, Maine to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Simpson Bay (average of $137). Flying from Portland, Maine to Simpson Bay in December is currently the most expensive (average of $345). 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated February 11, 2026.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Portland to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,179 reviews

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,179 reviews
Delta
7.9
Good
8,179 reviews

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,276 reviews
Delta
7.9
Good
8,179 reviews

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,267 reviews
Delta
7.9
Good
8,179 reviews

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

  • How long is the flight from Portland, Maine to Simpson Bay?

    Departing from Portland, Maine to Simpson Bay will take you 9h 20m. Portland, Maine and Simpson Bay are separated by a distance of 1817 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Portland, Maine to Simpson Bay round-trip?

    Currently priced at $113, Delta will fly you from Portland, Maine to Simpson Bay and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and American Airlines - these airlines can fly you to your destination from $305 and $566, respectively. Users have found that Delta is 84% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland, Maine to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Simpson Bay (average of $137). Flying from Portland, Maine to Simpson Bay in December is currently the most expensive (average of $345). 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 Portland to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Simpson Bay flights

Top 3 airlines flying from Portland to Simpson Bay

Discover the top 3 airlines that operate flights from Portland 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$113Average$595FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$566Average$652FlexibilityNo cancel feeOn-time71%

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