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 $696 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $804 and $811 round-trip. American Airlines is currently priced 16% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Portland to Simpson Bay one-way?

To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $405. Delta flights start at $730 while deals on Air Canada start at $896 one-way.

What is the cheapest day to fly from Portland to Simpson Bay?

Travelers seeking maximum savings on their Portland to Simpson Bay flight should consider departing on Thursday at noon when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from Portland to Simpson Bay?

Wednesday is generally a great day to depart. Flying on this day could help you save up to 63%.

What is the cheapest month to fly from Portland to Simpson Bay?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, August can be a great choice for travel to Simpson Bay. Flights to Simpson Bay from Portland in August are about $834 on average during August, but can be found for as low as $415.

Most accurate provider : When it comes to deals on Portland-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Simpson Bay flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Portland-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$251+ Flights from Portland to Simpson Bay

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1. Tell us where you want to go

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Cheap flight deals from Portland to Simpson Bay

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$671 (Mytrip)
One-way from	$251 (Kiwi.com)
Popular in	June
Cheapest in	August
Average price	$1,079

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 Portland to Simpson Bay Princess Juliana

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One-way flight from Portland to Simpson Bay Princess Juliana

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High demand for flights, 12% potential price rise

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Best time to find cheap flights, 2% potential price drop

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Average for round-trip flights in December 2024

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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 December 21, 2024.

Sun 12/227:11 pmPDX - SXM

2 stops38h 40mUnited Airlines

Sun 12/292:46 pmSXM - PDX

2 stops31h 56mUnited Airlines

Deal found 12/19

$1,231

Sun 12/2210:42 pmPDX - SXM

1 stop9h 48mAmerican Airlines

Sun 12/293:30 pmSXM - PDX

1 stop12h 08mAmerican Airlines

Deal found 12/19

$1,266

Best flights from Portland to Simpson Bay
Discover carefully curated flight deals from Portland to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 21, 2024.

Fri 1/105:30 pmPDX - SXM

2 stops17h 00mMultiple Airlines

Thu 1/164:10 pmSXM - PDX

3 stops28h 25mMultiple Airlines

Deal found 12/20

$671

Wed 3/1210:19 pmPDX - SXM

1 stop11h 51mAmerican Airlines

Wed 3/192:10 pmSXM - PDX

1 stop12h 02mAmerican Airlines

Deal found 12/20

$696

Fri 1/105:15 pmPDX - SXM

2 stops19h 05mDelta

Thu 1/161:40 pmSXM - PDX

1 stop12h 15mDelta

Deal found 12/20

$804

Tue 1/143:25 pmPDX - SXM

2 stops20h 50mAir Canada

Sun 1/264:55 pmSXM - PDX

2 stops25h 49mAir Canada

Deal found 12/20

$811

Fri 5/24:16 pmPDX - SXM

2 stops17h 13mUnited Airlines

Sat 5/103:55 pmSXM - PDX

2 stops20h 45mUnited Airlines

Deal found 12/20

$815

Last-minute flights from Portland to Simpson Bay
Discover last-minute flight deals from Portland to Simpson Bay. Data last updated December 21, 2024 and is based on user searches.

Fri 1/105:30 pmPDX - SXM

2 stops17h 00mMultiple Airlines

Thu 1/164:10 pmSXM - PDX

3 stops28h 25mMultiple Airlines

Deal found 12/20

$671

Fri 1/105:15 pmPDX - SXM

2 stops19h 05mDelta

Thu 1/161:40 pmSXM - PDX

1 stop12h 15mDelta

Deal found 12/20

$804

Fri 1/1010:45 pmPDX - SXM

1 stop13h 26mAmerican Airlines

Thu 1/163:20 pmSXM - PDX

1 stop12h 16mAmerican Airlines

Deal found 12/20

$816

Tue 1/143:25 pmPDX - SXM

2 stops20h 50mAir Canada

Sun 1/264:55 pmSXM - PDX

2 stops25h 49mAir Canada

Deal found 12/20

$811

Sat 1/181:32 pmPDX - SXM

2 stops22h 20mUnited Airlines

Sat 1/252:46 pmSXM - PDX

2 stops31h 19mUnited Airlines

Deal found 12/21

$956

One-way flights from Portland to Simpson Bay
Search for one-way flight options from Portland to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated December 21, 2024.

Tue 1/147:35 amPDX - SXM

3 stops26h 55mMultiple Airlines

Deal found 12/20

$251

Tue 1/1410:45 pmPDX - SXM

1 stop11h 27mAmerican Airlines

Deal found 12/20

$405

Fri 12/272:04 pmPDX - SXM

1 stop20h 16mDelta

Deal found 12/21

$730

Fri 12/273:25 pmPDX - SXM

2 stops21h 20mAir Canada

Deal found 12/21

$896

Find flights from Portland to Simpson Bay within your budget

Fly from

Fly to

Route

Depart

Return

Price

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 1/10

5:30 pm-2:30 pm

2 stops17h 00m

Simpson Bay Princess Juliana

Thu 1/16

4:10 pm-4:35 pm

3 stops28h 25m

$671

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 3/12

10:19 pm-1:10 pm

1 stop11h 51m

Simpson Bay Princess Juliana

Wed 3/19

2:10 pm-11:12 pm

1 stop12h 02m

$696

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 1/10

5:15 pm-4:20 pm

2 stops19h 05m

Simpson Bay Princess Juliana

Thu 1/16

1:40 pm-9:55 pm

1 stop12h 15m

$804

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 1/14

3:25 pm-4:15 pm

2 stops20h 50m

Simpson Bay Princess Juliana

Sun 1/26

4:55 pm-2:44 pm

2 stops25h 49m

$811

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 5/2

1:37 pm-12:29 pm

3 stops19h 52m

Simpson Bay Princess Juliana

Sat 5/10

3:55 pm-9:40 am

2 stops20h 45m

$815

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 1/14

7:35 am-2:30 pm

3 stops26h 55m

$251

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 1/14

10:45 pm-2:12 pm

1 stop11h 27m

$405

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 12/27

2:04 pm-2:20 pm

1 stop20h 16m

$730

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 12/27

3:25 pm-4:45 pm

2 stops21h 20m

$896

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Compare providers for flights from Portland to Simpson Bay

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Simpson Bay in December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
AranGrant	Price Accuracy3 stars	Trust Score*2 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Portland-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Simpson Bay flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Portland-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Travel insights for flights from Portland to Simpson Bay

Get recent, data-driven insights about flights from Portland to Simpson Bay including ideal travel times, pricing trends, and more.

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 $690). 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?

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

Delta

8.0

Very good

8,597 reviews

Reviews

1 / 10

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

Delta

8.0

Very good

8,597 reviews

Delta

8.0

Very good

8,597 reviews

Reviews

1 / 10

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

United Airlines

7.4

Good

9,035 reviews

Delta

8.0

Very good

8,597 reviews

Reviews

1 / 10

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

8,597 reviews

Reviews

1 / 10

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

Air Canada

7.0

Good

8,403 reviews

Delta

8.0

Very good

8,597 reviews

Reviews

1 / 10

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

Related info for your journey

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 $696 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $804 and $811 round-trip. American Airlines is currently priced 16% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Portland to Simpson Bay one-way?
To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $405. Delta flights start at $730 while deals on Air Canada start at $896 one-way.
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 $690). 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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Simpson Bay Princess Juliana Airport car rentals

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Top 2 airlines flying from Portland to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$495	Average$633	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$525	Average$890	FlexibilityNo cancel fee	On-time71%

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$251+ Cheap flights from Portland (PDX) 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Portland to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Portland to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Portland to Simpson Bay

Cheapest flights from Portland to Simpson BayExplore 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 December 21, 2024.

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 December 21, 2024.

Find flights from Portland to Simpson Bay within your budget

Compare providers for flights from Portland to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Simpson Bay in December.

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.

Travel insights for flights from Portland to Simpson Bay

Get recent, data-driven insights about flights from Portland to Simpson Bay including ideal travel times, pricing trends, and more.

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

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 December 21, 2024.

Reviews of airlines servicing Simpson Bay

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.

What are the cheapest airlines flying from Portland to Simpson Bay round-trip?

What are the cheapest airlines to fly from Portland to Simpson Bay one-way?

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

How can I find direct flights from Portland to Simpson Bay?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.

Top 2 airlines flying from Portland to Simpson Bay

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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 December 21, 2024.