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Simpson Bay

$581+ Cheap flights from Oregon 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
1 adult, Economy
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Cheap flight deals from Oregon to Simpson Bay

Cheapest flights from Oregon to Simpson Bay
Explore the most affordable flight options available from Oregon to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 15, 2026.

This Air Canada deal was found by Cheapflights users on 2/13. 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.
Wed 6/37:45 pm
PDX
-
SXM
2 stops15h 15m
Air Canada
Thu 6/113:05 pm
SXM
-
PDX
2 stops21h 25m
Air Canada
Deal found 2/13$581
This Air Canada deal was found by Cheapflights users on 2/12. 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 3/89:50 am
PDX
-
SXM
2 stops26h 10m
Air Canada
Mon 3/164:00 pm
SXM
-
PDX
2 stops44h 15m
Air Canada
Deal found 2/12$590
This Air Canada deal was found by Cheapflights users on 2/13. 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.
Wed 5/203:25 pm
PDX
-
SXM
2 stops19h 40m
Air Canada
Thu 5/282:55 pm
SXM
-
PDX
2 stops21h 35m
Air Canada
Deal found 2/13$598
This Air Canada deal was found by Cheapflights users on 2/13. 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 5/297:45 pm
PDX
-
SXM
2 stops15h 20m
Air Canada
Sat 6/63:05 pm
SXM
-
PDX
2 stops21h 25m
Air Canada
Deal found 2/13$617
This Air Canada deal was found by Cheapflights users on 2/13. 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.
Wed 5/137:45 pm
PDX
-
SXM
2 stops15h 20m
Air Canada
Thu 5/212:55 pm
SXM
-
PDX
2 stops21h 35m
Air Canada
Deal found 2/13$644
This Orbitz deal was found by Cheapflights users on 2/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:45 pm
PDX
-
SXM
2 stops39h 20m
Air Canada
Sat 5/232:55 pm
SXM
-
PDX
2 stops21h 35m
Air Canada
Deal found 2/14$650
This Air Canada deal was found by Cheapflights users on 2/11. 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.
Mon 3/23:15 pm
PDX
-
SXM
2 stops20h 45m
Air Canada
Mon 3/94:00 pm
SXM
-
PDX
2 stops44h 15m
Air Canada
Deal found 2/11$651
This Air Canada deal was found by Cheapflights users on 2/13. 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 5/87:45 pm
PDX
-
SXM
2 stops15h 20m
Air Canada
Sat 5/162:55 pm
SXM
-
PDX
2 stops21h 35m
Air Canada
Deal found 2/13$680
This Air Canada deal was found by Cheapflights users on 2/13. 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.
Wed 7/87:45 pm
PDX
-
SXM
2 stops15h 15m
Air Canada
Thu 7/163:05 pm
SXM
-
PDX
2 stops26h 46m
Air Canada
Deal found 2/13$686
This Air Canada deal was found by Cheapflights users on 2/13. 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.
Wed 5/67:45 pm
PDX
-
SXM
2 stops15h 20m
Air Canada
Thu 5/142:55 pm
SXM
-
PDX
2 stops21h 35m
Air Canada
Deal found 2/13$702
This FlightHub deal was found by Cheapflights users on 2/15. 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.
Wed 7/293:25 pm
PDX
-
SXM
2 stops19h 35m
Air Canada
Sat 8/83:05 pm
SXM
-
PDX
2 stops21h 26m
Air Canada
Deal found 2/15$706

Find flight deals from Oregon to Simpson Bay

Keep the following information in mind while searching for Oregon to Simpson Bay flight deals. Data was last updated February 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$581
(Air Canada)

Popular in

December

Cheapest in

June

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 Oregon 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 Oregon 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 February 15, 2026.
Use the filters below to find and compare flights from Oregon to Simpson Bay that are best for you.

Fly from

Oregon

Fly to

Simpson Bay

Route

Depart

Return

Price

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sun 3/8

9:50 am-3:00 pm

2 stops26h 10m

Simpson Bay Princess Juliana

Mon 3/16

4:00 pm-9:15 am

2 stops44h 15m

$590

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 7/29

3:25 pm-2:00 pm

2 stops19h 35m

Simpson Bay Princess Juliana

Sat 8/8

3:05 pm-9:31 am

2 stops21h 26m

$617

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 5/14

7:45 pm-2:05 pm

2 stops39h 20m

Simpson Bay Princess Juliana

Sat 5/23

2:55 pm-9:30 am

2 stops21h 35m

$650

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Mon 3/2

3:15 pm-4:00 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Mon 3/9

4:00 pm-9:15 am

2 stops44h 15m

$651

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Mon 5/25

9:39 pm-1:59 pm

1 stop13h 20m

Simpson Bay Princess Juliana

Wed 6/3

3:20 pm-9:57 am

2 stops21h 37m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 4/29

11:15 pm-12:33 pm

1 stop10h 18m

Simpson Bay Princess Juliana

Thu 5/7

1:35 pm-9:38 am

2 stops23h 03m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 5/5

11:06 pm-2:05 pm

1 stop11h 59m

Simpson Bay Princess Juliana

Thu 5/14

3:20 pm-8:45 am

2 stops20h 25m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 5/5

11:06 pm-2:05 pm

1 stop11h 59m

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-9:57 am

2 stops21h 37m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Mon 5/11

9:39 pm-1:59 pm

1 stop13h 20m

Simpson Bay Princess Juliana

Wed 5/20

3:20 pm-9:57 am

2 stops21h 37m

$730

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Best time to book a flight from Oregon to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Oregon 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 Oregon to Simpson Bay
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Oregon 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 airport do you fly into for flights to Simpson Bay from Oregon?

    If you book a flight to Simpson Bay from Oregon, you will be flying to Princess Juliana, which is the city’s only airport. Simpson Bay Princess Juliana (SXM) is located 0.5 mi from the center of Simpson Bay.

  • How long is the flight from Oregon to Simpson Bay?

    Air Canada can get you from Oregon to Simpson Bay in just under 26h 10m. Your travel time can differ by up to . There are 3867 mi between Oregon and Simpson Bay.

  • Can I find deals for flights from Oregon to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Oregon to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Simpson Bay.

  • Can I find deals for business class flights from Oregon to Simpson Bay?

    Yes. Cheapflights offers flight deals from Oregon 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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Alternative routes for Oregon to Simpson Bay

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Top airline flying from Oregon to Simpson Bay

Discover the top airline that operate flights from Oregon 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 February 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$712Average$842FlexibilityNo cancel feeOn-time71%

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