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Simpson Bay

$238+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
mar. 23 — mar. 301
lun. 3/23
lun. 3/30
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 febrero 21, 2026.

This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/87:45 pm
PDX
-
SXM
2 stops15h 20m
Air Canada
sáb. 5/162:55 pm
SXM
-
PDX
2 stops26h 50m
Air Canada
Deal found 2/18$604
This Air Canada deal was found by Cheapflights users on 2/18. 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.
lun. 3/27:05 pm
PDX
-
SXM
2 stops16h 55m
Air Canada
lun. 3/94:00 pm
SXM
-
PDX
2 stops20h 15m
Air Canada
Deal found 2/18$703
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/297:05 pm
PDX
-
SXM
2 stops15h 45m
Multiple Airlines
jue. 5/72:55 pm
SXM
-
PDX
2 stops26h 50m
Multiple Airlines
Deal found 2/21$729
This United Airlines deal was found by Cheapflights users on 2/19. 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.
mié. 4/294:15 pm
PDX
-
SXM
2 stops17h 18m
United Airlines
jue. 5/71:35 pm
SXM
-
PDX
2 stops23h 03m
United Airlines
Deal found 2/19$730
This American Airlines deal was found by Cheapflights users on 2/19. 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. 5/310:28 pm
PDX
-
SXM
1 stop13h 54m
American Airlines
mar. 6/22:53 pm
SXM
-
PDX
1 stop12h 03m
American Airlines
Deal found 2/19$745
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/296:05 pm
PDX
-
SXM
2 stops15h 05m
Delta
jue. 5/73:20 pm
SXM
-
PDX
2 stops20h 25m
Delta
Deal found 2/20$750
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2910:23 pm
PDX
-
SXM
1 stop11h 58m
American Airlines
jue. 5/74:35 pm
SXM
-
PDX
2 stops23h 23m
American Airlines
Deal found 2/20$755

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 febrero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$604
(Expedia)

One-way from

$238
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$847
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. 10% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 febrero 21, 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

vie. 5/8

3:25 pm-2:05 pm

2 stops19h 40m

Simpson Bay Princess Juliana

sáb. 5/16

2:55 pm-2:45 pm

2 stops26h 50m

$708

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mié. 4/29

11:15 pm-12:33 pm

1 stop10h 18m

Simpson Bay Princess Juliana

jue. 5/7

1:35 pm-9:38 am

2 stops23h 03m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

dom. 5/3

7:32 pm-2:05 pm

2 stops15h 33m

Simpson Bay Princess Juliana

mar. 6/2

3:20 pm-9:57 am

2 stops21h 37m

$750

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

vie. 5/1

10:28 pm-1:16 pm

1 stop11h 48m

Simpson Bay Princess Juliana

mié. 5/6

12:41 pm-11:53 pm

1 stop14h 12m

$770

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

vie. 5/8

3:25 pm-2:05 pm

3 stops19h 40m

Simpson Bay Princess Juliana

sáb. 5/16

2:55 pm-1:50 pm

3 stops25h 55m

$770

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

sáb. 5/9

10:23 pm-1:21 pm

1 stop11h 58m

Simpson Bay Princess Juliana

sáb. 5/16

12:41 pm-11:53 pm

1 stop14h 12m

$770

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mié. 4/29

1:52 pm-11:38 am

2 stops18h 46m

Simpson Bay Princess Juliana

jue. 5/7

12:41 pm-11:53 pm

1 stop14h 12m

$775

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mié. 7/22

11:30 pm-3:31 pm

2 stops13h 01m

Simpson Bay Princess Juliana

vie. 8/7

2:22 pm-10:44 am

2 stops23h 22m

$775

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mar. 3/31

9:43 am-1:30 pm

3 stops24h 47m

$238

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

lun. 3/23

10:30 pm-1:54 pm

1 stop12h 24m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 14 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 February.
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 febrero 21, 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
11,334 reviews

Comfort

7.2

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

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
11,334 reviews
American Airlines
7.2
Good
11,334 reviews

Comfort

7.2

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

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 10h 18m. Air Canada provides one of the quickest options available for as low as $730. The distance between Portland and Simpson Bay is about 3867 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 18% 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 febrero 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$712Average$842FlexibilityNo cancel feeOn-time71%

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