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Simpson Bay

$301+ Cheap flights from Portland (PDX) 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 28, 2025.

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.
Tue 12/210:45 pmPDX - SXM
1 stop13h 40mAmerican Airlines
Wed 12/103:20 pmSXM - PDX
1 stop12h 32mAmerican Airlines
Deal found 10/27$787
This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:00 pmPDX - SXM
2 stops39h 40mAir Canada
Tue 12/305:00 pmSXM - PDX
2 stops44h 15mAir Canada
Deal found 10/26$1,097
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 12/2212:49 amPDX - SXM
2 stops11h 44mAmerican Airlines
Tue 12/305:33 pmSXM - PDX
2 stops21h 08mAmerican Airlines
Deal found 10/26$1,101
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:00 pmPDX - SXM
2 stops39h 40mMultiple Airlines
Tue 12/303:40 pmSXM - PDX
3 stops29h 22mMultiple Airlines
Deal found 10/26$1,193
This Air Canada deal was found by Cheapflights users on 10/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/213:15 pmPDX - SXM
2 stops19h 25mAir Canada
Sat 11/293:40 pmSXM - PDX
2 stops45h 35mAir Canada
Deal found 10/26$2,282
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Fri 11/2110:15 pmPDX - SXM
1 stop11h 45mAmerican Airlines
Sat 11/295:05 pmSXM - PDX
2 stops22h 05mAmerican Airlines
Deal found 10/26$3,135
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2111:12 pmPDX - SXM
1 stop10h 23mUnited Airlines
Sat 11/292:40 pmSXM - PDX
1 stop25h 08mUnited Airlines
Deal found 10/26$4,515

Cheap flight deals from Portland to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$687
(American Airlines)

One-way from

$301
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$777
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.
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From Portland to Simpson Bay Princess Juliana
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One-way flight from Portland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 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 28, 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

PDX - SXM

PDXSXM

Portland

Tue 3/31

10:59 pm-3:10 pm

1 stop13h 11m

Simpson Bay Princess Juliana

Wed 4/8

2:25 pm-11:02 pm

1 stop11h 37m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 1/2

10:49 pm-4:33 pm

1 stop13h 44m

Simpson Bay Princess Juliana

Mon 1/12

5:33 pm-1:21 pm

2 stops23h 48m

$742

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 12/2

10:45 pm-4:25 pm

1 stop13h 40m

Simpson Bay Princess Juliana

Wed 12/10

3:20 pm-11:52 pm

1 stop12h 32m

$787

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 12/2

9:50 am-3:21 pm

3 stops25h 31m

$301

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 3/21

7:00 pm-1:40 pm

2 stops15h 40m

$418

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 3/20

3:15 pm-1:40 pm

2 stops43h 25m

$420

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 3/21

10:59 pm-2:20 pm

1 stop12h 21m

$454

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 3/21

3:15 pm-2:17 pm

3 stops20h 02m

$504

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 3/19

12:55 am-10:55 am

2 stops31h 00m

$718

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 3/20

10:59 pm-3:10 pm

1 stop13h 11m

$778

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 12 results
1
2

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*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice 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-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-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-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-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 to Simpson Bay?

Currently, January is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $443). Flying from Portland to Simpson Bay in December is currently the most expensive (average of $1,006). 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.

What is the cheapest time of day to fly from PDX to SXM?

Find hourly flight availability from Portland to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

When flying from Portland to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 43% versus a flight in the evening.

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 28, 2025.
See what other customers who have flown with Delta and American Airlines from Portland to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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
7,994 reviews
Delta
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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 to Simpson Bay?

    A quick flight from Portland to Simpson Bay can take about 11h 11m. American Airlines provides one of the quickest options available for as low as $687. The distance between Portland and Simpson Bay is about 3867 mi.

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

    Our cheapest airline available from Portland to Simpson Bay is American Airlines. Our recent data shows that you can find tickets from as low as $604 on this airline. An additional option worth looking into is Delta, starting at $687. American Airlines is currently priced 31% below the average price you’ll pay for this route.

  • 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 to Simpson Bay?

    Currently, January is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $443). Flying from Portland to Simpson Bay in December is currently the most expensive (average of $1,006). 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

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$604Average$853FlexibilityNo cancel feeOn-time71%
DeltaCheapest$687Average$926FlexibilityNo cancel feeOn-timeN/A

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