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Simpson Bay

$621+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$621
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$680
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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High demand for flights, 1% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 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 January 21, 2025.

This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/117:32 pmPDX - SXM
2 stops14h 56mMultiple Airlines
Sun 3/163:55 pmSXM - PDX
2 stops25h 49mMultiple Airlines
Deal found 1/20$621
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/77:32 pmPDX - SXM
2 stops14h 56mSpirit Airlines
Fri 3/142:33 pmSXM - PDX
3 stops31h 04mSpirit Airlines
Deal found 1/20$653
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1110:19 pmPDX - SXM
1 stop13h 56mAmerican Airlines
Sun 3/163:20 pmSXM - PDX
2 stops22h 40mAmerican Airlines
Deal found 1/20$800
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/210:43 pmPDX - SXM
1 stop13h 00mUnited Airlines
Sat 5/103:55 pmSXM - PDX
1 stop31h 07mUnited Airlines
Deal found 1/20$6,218

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/11

7:32 pm-1:28 pm

2 stops14h 56m

Simpson Bay Princess Juliana

Sun 3/16

3:55 pm-2:44 pm

2 stops25h 49m

$621

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 3/7

7:32 pm-2:28 pm

2 stops14h 56m

Simpson Bay Princess Juliana

Fri 3/14

2:33 pm-6:37 pm

3 stops31h 04m

$653

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/11

10:19 pm-3:15 pm

1 stop13h 56m

Simpson Bay Princess Juliana

Sun 3/16

3:20 pm-11:00 am

2 stops22h 40m

$800

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 5/2

10:43 pm-2:43 pm

1 stop13h 00m

Simpson Bay Princess Juliana

Sat 5/10

3:55 pm-8:02 pm

1 stop31h 07m

$6,218

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Portland-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 January 21, 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 January 21, 2025.
United Airlines
7.4
Good
8,984 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 10

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

United Airlines
7.4
Good
8,984 reviews
United Airlines
7.4
Good
8,984 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 10

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,984 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 10

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Spirit Airlines
6.3
Okay
8,113 reviews
United Airlines
7.4
Good
8,984 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 10

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 $653 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $800 and $6,218 round-trip. Spirit Airlines is currently priced 22% 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$495Average$645FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$530Average$910FlexibilityNo cancel feeOn-time71%
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