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Simpson Bay

$523+ Cheap flights from Portland (PDX) 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
feb. 27 — mar. 61
jue. 2/27
jue. 3/6
1 adult, Economy
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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 febrero 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$523
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$860
Provider with most accurate pricing for Portland-Simpson Bay Princess Juliana flight deals.
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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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Highest demand for flights based on searches. 5% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 febrero 22, 2025.

This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/27:01 pmPDX - SXM
2 stops15h 26mSpirit Airlines
sáb. 5/102:56 pmSXM - PDX
2 stops44h 16mSpirit Airlines
Deal found 2/22$523
This American Airlines deal was found by Cheapflights users on 2/21. 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.
dom. 9/711:10 pmPDX - SXM
1 stop11h 15mAmerican Airlines
sáb. 9/132:40 pmSXM - PDX
1 stop11h 20mAmerican Airlines
Deal found 2/21$708
This Delta deal was found by Cheapflights users on 2/21. 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.
dom. 9/75:10 pmPDX - SXM
2 stops17h 40mDelta
sáb. 9/133:15 pmSXM - PDX
2 stops20h 38mDelta
Deal found 2/21$713
This United deal was found by Cheapflights users on 2/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1111:38 pmPDX - SXM
1 stop10h 13mUnited Airlines
dom. 3/163:55 pmSXM - PDX
2 stops22h 59mUnited Airlines
Deal found 2/22$942
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/2112:16 pmPDX - SXM
1 stop25h 06mMultiple Airlines
vie. 3/288:12 amSXM - PDX
2 stops18h 32mMultiple Airlines
Deal found 2/20$1,708

Find flights from Portland to Simpson Bay within your budget

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 febrero 22, 2025.

Fly from

Portland

Fly to

Simpson Bay

Route

Depart

Return

Price

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

vie. 5/2

7:01 pm-1:27 pm

2 stops15h 26m

Simpson Bay Princess Juliana

sáb. 5/10

2:56 pm-8:12 am

2 stops44h 16m

$523

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

vie. 5/2

10:00 pm-11:05 am

1 stop10h 05m

Simpson Bay Princess Juliana

sáb. 5/10

3:24 pm-10:50 am

2 stops22h 26m

$738

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

dom. 6/15

9:45 pm-1:49 pm

1 stop13h 04m

Simpson Bay Princess Juliana

vie. 6/27

3:10 pm-12:19 am

1 stop12h 09m

$818

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mar. 3/11

8:55 am-12:51 pm

2 stops24h 56m

Simpson Bay Princess Juliana

dom. 3/16

3:55 pm-12:37 pm

2 stops23h 42m

$942

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

vie. 3/21

12:16 pm-4:22 pm

1 stop25h 06m

Simpson Bay Princess Juliana

vie. 3/28

8:12 am-11:44 pm

2 stops18h 32m

$1,708

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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 Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 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-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.

Travel insights for flights from Portland to Simpson Bay

Get recent, data-driven insights about flights from Portland to Simpson Bay including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $459). Flying from Portland to Simpson Bay in July is currently the most expensive (average of $684). 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 febrero 22, 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 30% versus a flight in the afternoon.

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 febrero 22, 2025.
Delta
8.0
Very good
8,203 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,203 reviews
Delta
8.0
Very good
8,203 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,754 reviews
Delta
8.0
Very good
8,203 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,203 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Spirit Airlines
6.3
Okay
8,012 reviews
Delta
8.0
Very good
8,203 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    Our cheapest airline available from Portland to Simpson Bay is Spirit Airlines. Our recent data shows that you can find tickets from as low as $523 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $738 and $818 round-trip. Spirit Airlines is currently priced 35% 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, September is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $459). Flying from Portland to Simpson Bay in July is currently the most expensive (average of $684). 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

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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 febrero 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$495Average$712FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$530Average$866FlexibilityNo cancel feeOn-time71%
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