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Simpson Bay

$269+ Cheap flights from Oregon 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$416
(Priceline)

One-way from

$269
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$742
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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One-way flight from Oregon to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 4% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/165:40 pmPDX - SXM
2 stops17h 20mSpirit Airlines
Fri 5/233:05 pmSXM - PDX
2 stops24h 37mSpirit Airlines
Deal found 4/30$416
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/101:45 pmPDX - SXM
2 stops44h 30mMultiple Airlines
Wed 6/183:05 pmSXM - PDX
2 stops23h 12mMultiple Airlines
Deal found 4/30$565
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 6/1011:00 pmPDX - SXM
1 stop12h 00mDelta
Wed 6/183:25 pmSXM - PDX
1 stop11h 34mDelta
Deal found 4/30$687
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 12/611:08 pmPDX - SXM
1 stop12h 32mAmerican Airlines
Mon 12/153:15 pmSXM - PDX
2 stops22h 55mAmerican Airlines
Deal found 4/30$713
This WestJet deal was found by Cheapflights users on 4/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/101:45 pmPDX - SXM
2 stops44h 30mWestJet
Thu 6/192:10 pmSXM - PDX
2 stops49h 42mWestJet
Deal found 4/30$758
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/108:30 amPDX - SXM
2 stops24h 59mUnited Airlines
Wed 6/183:55 pmSXM - PDX
2 stops20h 47mUnited Airlines
Deal found 4/30$782

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 May 1, 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

Fri 5/16

5:40 pm-2:00 pm

2 stops17h 20m

Simpson Bay Princess Juliana

Fri 5/23

3:05 pm-12:42 pm

2 stops24h 37m

$416

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 6/10

1:45 pm-1:15 pm

2 stops44h 30m

Simpson Bay Princess Juliana

Wed 6/18

3:05 pm-11:17 am

2 stops23h 12m

$565

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 6/10

11:00 pm-2:00 pm

1 stop12h 00m

Simpson Bay Princess Juliana

Wed 6/18

3:25 pm-11:59 pm

1 stop11h 34m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 6/10

1:45 pm-1:15 pm

2 stops44h 30m

Simpson Bay Princess Juliana

Thu 6/19

2:10 pm-12:52 pm

2 stops49h 42m

$758

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 6/12

5:36 pm-3:05 pm

2 stops18h 29m

Simpson Bay Princess Juliana

Thu 6/19

2:20 pm-5:48 pm

1 stop30h 28m

$771

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 6/10

8:30 am-12:29 pm

2 stops24h 59m

Simpson Bay Princess Juliana

Wed 6/18

3:55 pm-9:42 am

2 stops20h 47m

$782

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 6/4

5:40 pm-1:15 pm

2 stops16h 35m

$269

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 6/4

10:55 pm-12:29 pm

1 stop10h 34m

$388

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 6/3

12:40 am-1:19 pm

2 stops33h 39m

$1,835

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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, September is the cheapest month in which you can book a flight from Oregon to Simpson Bay (average of $459). Flying from Oregon to Simpson Bay in July is currently the most expensive (average of $669). 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 May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Simpson Bay as you normally would.

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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,826 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Spirit Airlines
6.3
Okay
7,963 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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, September is the cheapest month in which you can book a flight from Oregon to Simpson Bay (average of $459). Flying from Oregon to Simpson Bay in July is currently the most expensive (average of $669). 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

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Alternative routes for Oregon to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$495Average$872FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$595Average$848FlexibilityNo cancel feeOn-time71%

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