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Simpson Bay

$641+ Cheap flights from Portland (PDX) 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$641
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$695
From Portland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Air Canada deal was found by Cheapflights users on 9/10. 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.
Sat 12/67:00 pmPDX - SXM
2 stops41h 00mAir Canada
Mon 12/155:00 pmSXM - PDX
2 stops25h 45mAir Canada
Deal found 9/10$641
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/610:45 pmPDX - SXM
1 stop11h 35mAmerican Airlines
Mon 12/153:20 pmSXM - PDX
1 stop12h 32mAmerican Airlines
Deal found 9/10$712
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/2411:58 pmPDX - SXM
2 stops12h 17mAmerican Airlines
Sat 11/14:24 pmSXM - PDX
2 stops22h 46mAmerican Airlines
Deal found 9/10$742
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:25 pmPDX - SXM
2 stops41h 32mUnited Airlines
Sat 11/11:20 pmSXM - PDX
3 stops25h 38mUnited Airlines
Deal found 9/11$874
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:02 pmPDX - SXM
2 stops17h 16mUnited Airlines
Mon 12/152:52 pmSXM - PDX
3 stops24h 11mUnited Airlines
Deal found 9/11$1,015

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 September 11, 2025.
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

Sat 12/6

10:45 pm-2:20 pm

1 stop11h 35m

Simpson Bay Princess Juliana

Mon 12/15

3:20 pm-11:52 pm

1 stop12h 32m

$712

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 10/24

11:58 pm-3:15 pm

2 stops12h 17m

Simpson Bay Princess Juliana

Sat 11/1

4:24 pm-12:10 pm

2 stops22h 46m

$742

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 2/27

11:11 pm-3:10 pm

1 stop11h 59m

Simpson Bay Princess Juliana

Sat 3/7

5:42 pm-9:06 am

2 stops19h 24m

$805

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 10/24

6:25 pm-2:57 pm

2 stops41h 32m

Simpson Bay Princess Juliana

Sat 11/1

1:20 pm-10:33 pm

1 stop12h 13m

$874

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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

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

Currently, September is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $459). Flying from Portland to Simpson Bay in March is currently the most expensive (average of $652). 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 PDX to SXM?

Find hourly flight availability from Portland 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 September 11, 2025.

When flying from Portland to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 30% versus a flight in the afternoon.

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 September 11, 2025.
See what other customers who have flown with Delta and 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.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 11h 35m. American Airlines provides one of the quickest options available for as low as $712. The distance between Portland and Simpson Bay is about 3867 mi.

  • What are the cheapest airlines flying 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 $604 on this airline. An additional option worth looking into is Delta, starting at $645. American Airlines is currently priced 29% 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.

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

    Currently, September is the cheapest month in which you can book a flight from Portland to Simpson Bay (average of $459). Flying from Portland to Simpson Bay in March is currently the most expensive (average of $652). 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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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 2 airlines flying from Portland to Simpson Bay

Discover the top 2 airlines 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$604Average$846FlexibilityNo cancel feeOn-time71%
DeltaCheapest$645Average$926FlexibilityNo cancel feeOn-timeN/A

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