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Simpson Bay

$629+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
ene. 15 — ene. 221
jue. 1/15
jue. 1/22
1 adult, Economy
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Cheap flight deals from Oregon to Simpson Bay

Best flights from Oregon to Simpson Bay
Discover carefully curated flight deals from Oregon to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 16, 2025.

This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/267:00 pmPDX - SXM
2 stops17h 00mAir Canada
jue. 1/293:40 pmSXM - PDX
2 stops30h 50mAir Canada
Deal found 12/15$629
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:53 pmPDX - SXM
1 stop9h 36mAmerican Airlines
mié. 4/82:25 pmSXM - PDX
1 stop11h 37mAmerican Airlines
Deal found 12/15$687
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/291:00 pmPDX - SXM
2 stops20h 18mDelta
jue. 5/73:20 pmSXM - PDX
2 stops20h 16mDelta
Deal found 12/15$692
This Air Canada deal was found by Cheapflights users on 12/16. 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.
jue. 3/57:05 pmPDX - SXM
2 stops16h 55mAir Canada
dom. 3/152:40 pmSXM - PDX
2 stops45h 35mAir Canada
Deal found 12/16$677
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:35 pmPDX - SXM
2 stops13h 53mAmerican Airlines
mar. 4/72:25 pmSXM - PDX
1 stop11h 37mAmerican Airlines
Deal found 12/15$692
This Air Canada deal was found by Cheapflights users on 12/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/227:05 pmPDX - SXM
2 stops16h 55mAir Canada
lun. 3/25:00 pmSXM - PDX
2 stops25h 40mAir Canada
Deal found 12/15$686

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 diciembre 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$629
(Air Canada)

Popular in

December

Cheapest in

September

Average price

$1,372
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 Oregon to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 diciembre 16, 2025.
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

lun. 1/26

7:00 pm-4:00 pm

2 stops17h 00m

Simpson Bay Princess Juliana

jue. 1/29

3:40 pm-6:30 pm

2 stops30h 50m

$629

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

jue. 3/5

7:05 pm-4:00 pm

2 stops16h 55m

Simpson Bay Princess Juliana

dom. 3/15

2:40 pm-9:15 am

2 stops45h 35m

$677

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

dom. 2/22

7:05 pm-4:00 pm

2 stops16h 55m

Simpson Bay Princess Juliana

lun. 3/2

5:00 pm-2:40 pm

2 stops25h 40m

$686

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mar. 3/31

10:53 pm-11:29 am

1 stop9h 36m

Simpson Bay Princess Juliana

mié. 4/8

2:25 pm-11:02 pm

1 stop11h 37m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mié. 4/29

1:00 pm-12:18 pm

2 stops20h 18m

Simpson Bay Princess Juliana

jue. 5/7

3:20 pm-8:36 am

2 stops20h 16m

$692

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

mar. 3/31

10:35 pm-3:28 pm

2 stops13h 53m

Simpson Bay Princess Juliana

mar. 4/7

2:25 pm-11:02 pm

1 stop11h 37m

$692

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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

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

Currently, January is the cheapest month in which you can book a flight from Oregon to Simpson Bay (average of $470). Flying from Oregon to Simpson Bay in December is currently the most expensive (average of $1,203). 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 OR to SXM?

Find hourly flight availability from Oregon 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 diciembre 16, 2025.

It’s typically best to fly out from Oregon to Simpson Bay in the morning. Doing so could potentially save you 24% on the flight price compared to flying in the evening, which is usually more expensive.

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 and American Airlines can get you from Oregon to Simpson Bay in just under 9h 36m. Your travel time can differ by up to 7h 24m. There are 3867 mi between Oregon and Simpson Bay. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Oregon to Simpson Bay (average of $470). Flying from Oregon to Simpson Bay in December is currently the most expensive (average of $1,203). 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

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 2 airlines flying from Oregon to Simpson Bay

Discover the top 2 airlines 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 diciembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$687Average$926FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$712Average$859FlexibilityNo cancel feeOn-time71%

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