HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$256+ Cheap flights from Portland, ME (PWM) 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Portland to Simpson Bay

Best flights from Portland to Simpson Bay
Discover carefully curated flight deals from Portland to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 27, 2025.

This American Airlines deal was found by Cheapflights users on 12/24. 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 1/226:00 amPWM - SXM
1 stop7h 31mAmerican Airlines
Thu 1/293:31 pmSXM - PWM
2 stops21h 35mAmerican Airlines
Deal found 12/24$298
This Priceline deal was found by Cheapflights users on 12/25. 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.
Tue 3/316:00 amPWM - SXM
1 stop7h 39mJetBlue
Tue 4/73:00 pmSXM - PWM
1 stop8h 47mJetBlue
Deal found 12/25$371
This American Airlines deal was found by Cheapflights users on 12/25. 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 3/315:07 pmPWM - SXM
2 stops20h 09mAmerican Airlines
Mon 4/64:28 pmSXM - PWM
2 stops20h 59mAmerican Airlines
Deal found 12/25$322
This American Airlines deal was found by Cheapflights users on 12/25. 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 4/25:38 pmPWM - SXM
2 stops21h 50mAmerican Airlines
Wed 4/83:55 pmSXM - PWM
2 stops20h 05mAmerican Airlines
Deal found 12/25$346
This Priceline deal was found by Cheapflights users on 12/25. 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.
Tue 3/316:00 amPWM - SXM
1 stop9h 20mJetBlue
Mon 4/63:00 pmSXM - PWM
1 stop8h 47mJetBlue
Deal found 12/25$401
This American Airlines deal was found by Cheapflights users on 12/26. 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 3/85:38 pmPWM - SXM
2 stops21h 50mAmerican Airlines
Sun 3/1512:29 pmSXM - PWM
2 stops23h 50mAmerican Airlines
Deal found 12/26$454
This Priceline deal was found by Cheapflights users on 12/25. 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 4/26:00 amPWM - SXM
1 stop9h 20mJetBlue
Wed 4/83:00 pmSXM - PWM
1 stop8h 47mJetBlue
Deal found 12/25$501
This American Airlines deal was found by Cheapflights users on 12/26. 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 4/155:27 pmPWM - SXM
2 stops19h 18mAmerican Airlines
Wed 4/223:55 pmSXM - PWM
2 stops20h 05mAmerican Airlines
Deal found 12/26$532

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 December 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$293
(American Airlines)

One-way from

$256
(Delta)

Popular in

July

Cheapest in

September

Average price

$1,005
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
One-way flight from Portland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($175 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($52 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 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 December 27, 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

Thu 1/22

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Thu 1/29

3:31 pm-12:06 pm

2 stops21h 35m

$298

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 3/31

5:07 pm-1:16 pm

2 stops20h 09m

Simpson Bay Princess Juliana

Mon 4/6

4:28 pm-1:27 pm

2 stops20h 59m

$322

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 4/2

5:38 pm-3:28 pm

2 stops21h 50m

Simpson Bay Princess Juliana

Wed 4/8

3:55 pm-12:00 pm

2 stops20h 05m

$346

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 3/31

6:00 am-1:39 pm

1 stop7h 39m

Simpson Bay Princess Juliana

Tue 4/7

3:00 pm-11:47 pm

1 stop8h 47m

$371

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 3/31

6:00 am-3:20 pm

1 stop9h 20m

Simpson Bay Princess Juliana

Mon 4/6

3:00 pm-11:47 pm

1 stop8h 47m

$401

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 3/8

5:38 pm-3:28 pm

2 stops21h 50m

Simpson Bay Princess Juliana

Sun 3/15

12:29 pm-12:19 pm

2 stops23h 50m

$454

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 4/2

6:00 am-3:20 pm

1 stop9h 20m

Simpson Bay Princess Juliana

Wed 4/8

3:00 pm-11:47 pm

1 stop8h 47m

$501

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 4/15

5:27 pm-12:45 pm

2 stops19h 18m

Simpson Bay Princess Juliana

Wed 4/22

3:55 pm-12:00 pm

2 stops20h 05m

$532

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 3/28

5:18 am-3:08 pm

1 stop9h 50m

$256

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 3/28

5:57 pm-3:28 pm

2 stops21h 31m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 December.
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 December 27, 2025.
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
8,018 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

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
8,018 reviews
Delta
7.9
Good
8,018 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

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
9,116 reviews
Delta
7.9
Good
8,018 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

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
11,067 reviews
Delta
7.9
Good
8,018 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

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 7h 31m. 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 $268, 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 64% 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$794FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$631FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$566Average$660FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights