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Simpson Bay

$687+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$687
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$777
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
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Highest demand for flights based on searches. 7% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This Air Canada deal was found by Cheapflights users on 10/29. 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 11/213:15 pmPDX - SXM
2 stops19h 25mAir Canada
Sat 11/293:40 pmSXM - PDX
2 stops45h 35mAir Canada
Deal found 10/29$2,282
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 11/2110:10 pmPDX - SXM
1 stop12h 45mDelta
Sat 11/294:30 pmSXM - PDX
2 stops24h 48mDelta
Deal found 10/29$2,858
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/2111:59 pmPDX - SXM
1 stop11h 58mUnited Airlines
Sat 11/292:40 pmSXM - PDX
1 stop25h 08mUnited Airlines
Deal found 10/29$4,515

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 October 30, 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

Tue 3/31

10:59 pm-3:10 pm

1 stop13h 11m

Simpson Bay Princess Juliana

Wed 4/8

2:25 pm-11:02 pm

1 stop11h 37m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 2/7

10:15 pm-1:45 pm

1 stop11h 30m

Simpson Bay Princess Juliana

Sun 2/15

1:41 pm-11:59 pm

1 stop14h 18m

$717

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 $443). Flying from Oregon to Simpson Bay in December is currently the most expensive (average of $1,006). 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 October 30, 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?

    American Airlines can get you from Oregon to Simpson Bay in just under 13h 11m. 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.

  • 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 $443). Flying from Oregon to Simpson Bay in December is currently the most expensive (average of $1,006). 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$604Average$853FlexibilityNo cancel feeOn-time71%
DeltaCheapest$687Average$926FlexibilityNo cancel feeOn-timeN/A

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