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Simpson Bay

$555+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:05 pm
PDX
-
SXM
2 stops16h 55m
Air Canada
Mon 3/94:00 pm
SXM
-
PDX
2 stops25h 40m
Air Canada
Deal found 1/27$555
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:05 pm
PDX
-
SXM
2 stops40h 55m
Air Canada
Wed 2/255:00 pm
SXM
-
PDX
2 stops29h 30m
Air Canada
Deal found 1/28$658
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:50 am
PDX
-
SXM
2 stops26h 10m
Air Canada
Tue 3/104:00 pm
SXM
-
PDX
2 stops25h 40m
Air Canada
Deal found 1/28$678
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/319:50 am
PDX
-
SXM
2 stops26h 00m
Air Canada
Tue 4/72:40 pm
SXM
-
PDX
2 stops30h 50m
Air Canada
Deal found 1/28$687
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/3110:53 pm
PDX
-
SXM
1 stop9h 36m
American Airlines
Tue 4/72:21 pm
SXM
-
PDX
1 stop12h 31m
American Airlines
Deal found 1/27$715
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:50 pm
PDX
-
SXM
2 stops20h 43m
United Airlines
Thu 5/71:35 pm
SXM
-
PDX
2 stops23h 03m
United Airlines
Deal found 1/28$726
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/210:53 pm
PDX
-
SXM
1 stop13h 35m
American Airlines
Mon 3/912:29 pm
SXM
-
PDX
1 stop14h 15m
American Airlines
Deal found 1/28$740
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/291:55 pm
PDX
-
SXM
2 stops18h 42m
American Airlines
Thu 5/74:35 pm
SXM
-
PDX
2 stops21h 26m
American Airlines
Deal found 1/27$745

Find 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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$555
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$747
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. 10% potential increase in price ($107 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Mon 3/2

7:05 pm-4:00 pm

2 stops16h 55m

Simpson Bay Princess Juliana

Mon 3/9

4:00 pm-2:40 pm

2 stops25h 40m

$555

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sun 2/22

7:05 pm-4:00 pm

2 stops40h 55m

Simpson Bay Princess Juliana

Wed 2/25

5:00 pm-9:15 am

2 stops44h 15m

$658

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/3

9:50 am-4:00 pm

2 stops26h 10m

Simpson Bay Princess Juliana

Tue 3/10

4:00 pm-2:40 pm

2 stops25h 40m

$678

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/31

9:50 am-2:50 pm

2 stops26h 00m

Simpson Bay Princess Juliana

Tue 4/7

2:40 pm-6:30 pm

2 stops30h 50m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/3

9:45 pm-2:50 pm

1 stop13h 05m

Simpson Bay Princess Juliana

Tue 3/10

12:55 pm-10:08 pm

1 stop12h 13m

$715

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/31

10:53 pm-11:29 am

1 stop9h 36m

Simpson Bay Princess Juliana

Tue 4/7

2:21 pm-11:52 pm

1 stop12h 31m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Simpson Bay

How much does it cost to fly round-trip from Portland to Simpson Bay?

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 29, 2026.
See what other customers who have flown with 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.
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 16h 55m. Air Canada provides one of the quickest options available for as low as $555. The distance between Portland and Simpson Bay is about 3867 mi.

  • What is the cheapest airline to fly 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 $712 on this airline. American Airlines is currently priced 21% 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.

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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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 airline flying from Portland to Simpson Bay

Discover the top airline 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$712Average$842FlexibilityNo cancel feeOn-time71%

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