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Simpson Bay

$537+ Cheap flights from Portland, ME (PWM) 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 (PWM) 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 July 2, 2025.

Round-trip from

$537
(Delta)

Popular in

August

Cheapest in

September
From Portland to Simpson Bay Princess Juliana
Search Deals
High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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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 July 2, 2025.

This Delta deal was found by Cheapflights users on 7/2. 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.
Sun 12/145:40 amPWM - SXM
1 stop7h 55mDelta
Tue 12/234:25 pmSXM - PWM
1 stop8h 06mDelta
Deal found 7/2$537
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 12/145:06 pmPWM - SXM
2 stops21h 34mAmerican Airlines
Tue 12/233:30 pmSXM - PWM
1 stop10h 07mAmerican Airlines
Deal found 7/2$542
This JetBlue deal was found by Cheapflights users on 7/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:10 amPWM - SXM
1 stop7h 21mJetBlue
Sat 7/2612:25 pmSXM - PWM
1 stop11h 52mJetBlue
Deal found 7/1$612
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/16:05 pmPWM - SXM
2 stops19h 55mMultiple Airlines
Fri 8/83:05 pmSXM - PWM
3 stops28h 22mMultiple Airlines
Deal found 7/2$848

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 July 2, 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

PWM - SXM

PWMSXM

Portland

Sun 12/14

5:40 am-2:35 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Tue 12/23

4:25 pm-11:31 pm

1 stop8h 06m

$537

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 12/14

5:06 pm-3:40 pm

2 stops21h 34m

Simpson Bay Princess Juliana

Tue 12/23

3:30 pm-12:37 am

1 stop10h 07m

$542

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 7/21

6:10 am-1:31 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Sat 7/26

12:25 pm-12:17 am

1 stop11h 52m

$612

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 8/1

6:05 pm-2:00 pm

2 stops19h 55m

Simpson Bay Princess Juliana

Fri 8/8

3:05 pm-7:27 pm

3 stops28h 22m

$848

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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, Maine to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Simpson Bay (average of $459). Flying from Portland, Maine to Simpson Bay in March is currently the most expensive (average of $656). 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.

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 July 2, 2025.
Get a feel of what it's like to fly with Delta, JetBlue, and American Airlines from Portland to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

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
7,983 reviews
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

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!
JetBlue
7.3
Good
2,918 reviews
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

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
7,983 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

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.

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

    Currently priced at $537, Delta will fly you from Portland, Maine to Simpson Bay and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and JetBlue - these airlines can fly you to your destination from $542 and $612, respectively. Users have found that Delta is 25% cheaper than the other options available to this destination.

  • 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, Maine to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Simpson Bay (average of $459). Flying from Portland, Maine to Simpson Bay in March is currently the most expensive (average of $656). 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 Portland to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Simpson Bay flights

Top 3 airlines flying from Portland to Simpson Bay

Discover the top 3 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$286Average$689FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$540Average$780FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$566Average$788FlexibilityNo cancel feeOn-time71%

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