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Simpson Bay

$316+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find 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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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
Thu 11/204:20 pmSXM - PWM
2 stops24h 47mDelta
Deal found 10/28$316
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/157:02 amPWM - SXM
1 stop29h 58mAmerican Airlines
Thu 11/202:51 pmSXM - PWM
1 stop8h 42mAmerican Airlines
Deal found 10/28$319
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/45:17 pmPWM - SXM
2 stops22h 08mAmerican Airlines
Fri 12/123:20 pmSXM - PWM
2 stops21h 15mAmerican Airlines
Deal found 10/28$376
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/45:17 pmPWM - SXM
2 stops22h 08mAmerican Airlines
Thu 12/113:20 pmSXM - PWM
2 stops33h 17mAmerican Airlines
Deal found 10/28$391
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/115:17 pmPWM - SXM
2 stops19h 35mAmerican Airlines
Thu 12/185:33 pmSXM - PWM
2 stops19h 16mAmerican Airlines
Deal found 10/27$469
This Delta deal was found by Cheapflights users on 10/28. 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 12/36:15 amPWM - SXM
2 stops31h 13mDelta
Thu 12/113:53 pmSXM - PWM
2 stops21h 20mDelta
Deal found 10/28$514
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/35:43 amPWM - SXM
2 stops9h 39mAmerican Airlines
Fri 11/142:51 pmSXM - PWM
2 stops21h 55mAmerican Airlines
Deal found 10/29$517
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/16:37 pmPWM - SXM
2 stops20h 45mAmerican Airlines
Wed 12/105:25 pmSXM - PWM
2 stops24h 03mAmerican Airlines
Deal found 10/28$554
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/16:37 pmPWM - SXM
2 stops20h 45mAmerican Airlines
Thu 12/113:20 pmSXM - PWM
2 stops33h 17mAmerican Airlines
Deal found 10/28$569
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/47:11 amPWM - SXM
1 stop29h 41mAmerican Airlines
Wed 12/105:25 pmSXM - PWM
2 stops24h 03mAmerican Airlines
Deal found 10/28$583

Cheap 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$316
(Delta)

Popular in

July

Cheapest in

September

Average price

$723
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. 19% potential increase in price ($181 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($53 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 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 October 29, 2025.
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

Sat 11/15

6:35 am-2:05 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Thu 11/20

4:20 pm-4:07 pm

2 stops24h 47m

$316

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 12/11

4:53 pm-2:28 pm

2 stops20h 35m

Simpson Bay Princess Juliana

Thu 12/18

1:45 pm-10:23 pm

1 stop9h 38m

$316

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 11/15

7:02 am-2:00 pm

1 stop29h 58m

Simpson Bay Princess Juliana

Thu 11/20

2:51 pm-10:33 pm

1 stop8h 42m

$319

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

12:46 pm-12:58 pm

2 stops23h 12m

Simpson Bay Princess Juliana

Sun 1/11

3:50 pm-10:54 pm

1 stop8h 04m

$367

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 12/5

5:17 pm-12:10 pm

2 stops17h 53m

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-11:35 am

2 stops21h 15m

$376

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 12/5

5:17 pm-12:10 pm

2 stops17h 53m

Simpson Bay Princess Juliana

Thu 12/11

3:20 pm-11:37 pm

2 stops33h 17m

$391

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:30 am-1:53 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Wed 4/1

12:45 pm-9:59 pm

1 stop9h 14m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $143). Flying from Portland, Maine to Simpson Bay in June is currently the most expensive (average of $372). 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 October 29, 2025.
Get a feel of what it's like to fly with Delta and United 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
7,992 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 6h 30m. 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 $286, 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. Check Cheapflights for deals on United Airlines for as low as $540. Users have found that Delta is 61% 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 $143). Flying from Portland, Maine to Simpson Bay in June is currently the most expensive (average of $372). 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 2 airlines flying from Portland to Simpson Bay

Discover the top 2 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$286Average$794FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$540Average$633FlexibilityNo cancel feeOn-time69%

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