$463+ Cheap flights from Portland, ME (PWM) to St. Maarten
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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SXM
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Best
Cheapest flights from Portland to St. MaartenExplore the most affordable flight options available from Portland to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
Explore the most affordable flight options available from Portland to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 12/16:47 pm -
2 stops20h 44m
Tue 12/153:26 pm -
2 stops21h 27m
Deal found 8/18![American Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 8/22. 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 10/275:50 am -
1 stop7h 00m
Fri 10/301:52 pm -
1 stop9h 29m
Deal found 8/22![United Airlines logo]()
$495
This Priceline deal was found by Cheapflights users on 8/20. 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.
Sun 10/46:00 am -
1 stop7h 23m
Sun 10/112:45 pm -
1 stop9h 07m
Deal found 8/20![JetBlue logo]()
$517
This American Airlines deal was found by Cheapflights users on 8/21. 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 10/35:06 pm -
2 stops20h 17m
Thu 10/84:39 pm -
2 stops23h 30m
Deal found 8/21![American Airlines logo]()
$566
This JetBlue deal was found by Cheapflights users on 8/18. 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 10/56:00 am -
1 stop7h 23m
Fri 10/92:45 pm -
1 stop9h 07m
Deal found 8/18![JetBlue logo]()
$601
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/46:00 pm -
2 stops21h 39m
Sun 10/114:39 pm -
2 stops23h 00m
Deal found 8/20![American Airlines logo]()
$683
This JetBlue deal was found by Cheapflights users on 8/21. 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 10/56:00 am -
1 stop7h 23m
Mon 10/122:45 pm -
1 stop9h 07m
Deal found 8/21![JetBlue logo]()
$711
Best flights from Portland to St. MaartenDiscover carefully curated flight deals from Portland to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
Discover carefully curated flight deals from Portland to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Mon 2/15:08 pm -
2 stops22h 20m
Mon 2/82:03 pm -
2 stops10h 37m
Deal found 8/21![American Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/275:50 am -
1 stop7h 00m
Fri 10/301:52 pm -
1 stop9h 29m
Deal found 8/21![United Airlines logo]()
$495
This JetBlue deal was found by Cheapflights users on 8/20. 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 10/56:00 am -
1 stop7h 23m
Fri 10/92:45 pm -
1 stop9h 07m
Deal found 8/20![JetBlue logo]()
$601
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 12/16:47 pm -
2 stops20h 44m
Tue 12/153:26 pm -
2 stops21h 27m
Deal found 8/20![American Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/35:06 pm -
2 stops20h 17m
Thu 10/84:39 pm -
2 stops23h 30m
Deal found 8/18![American Airlines logo]()
$625
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/46:00 pm -
2 stops21h 39m
Sun 10/114:39 pm -
2 stops23h 00m
Deal found 8/20![American Airlines logo]()
$683
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 2/156:28 pm -
2 stops18h 51m
Mon 2/223:20 pm -
2 stops21h 52m
Deal found 8/18![American Airlines logo]()
$710
Find flight deals from Portland to St. Maarten
Keep the following information in mind while searching for Portland to St. Maarten flight deals. Data was last updated August 23, 2026.
Round-trip from | $463 (American Airlines) |
|---|
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to St. Maarten 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 7,457,451 searches. Data last updated August 23, 2026.
Use the filters below to find and compare flights from Portland to St. Maarten that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Mon 2/1
5:08 pm-4:28 pm
2 stops22h 20m
Simpson Bay Princess Juliana
Mon 2/8
2:03 pm-11:40 pm
2 stops10h 37m
$481
Quickest round-trip
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Tue 10/27
5:50 am-12:50 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Fri 10/30
1:52 pm-11:21 pm
1 stop9h 29m
$495
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Tue 12/1
6:47 pm-4:31 pm
2 stops20h 44m
Simpson Bay Princess Juliana
Tue 12/15
3:26 pm-11:53 am
2 stops21h 27m
$510
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Mon 10/5
6:00 am-1:23 pm
1 stop7h 23m
Simpson Bay Princess Juliana
Fri 10/9
2:45 pm-11:52 pm
1 stop9h 07m
$601
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Sat 10/3
5:06 pm-1:23 pm
2 stops20h 17m
Simpson Bay Princess Juliana
Thu 10/8
4:39 pm-4:09 pm
2 stops23h 30m
$625
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Sun 10/4
6:00 pm-3:39 pm
2 stops21h 39m
Simpson Bay Princess Juliana
Sun 10/11
4:39 pm-3:39 pm
2 stops23h 00m
$683
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Mon 2/15
6:28 pm-2:19 pm
2 stops18h 51m
Simpson Bay Princess Juliana
Mon 2/22
3:20 pm-12:12 pm
2 stops21h 52m
$710
Sorted by cheapest first
Best time to book a flight from Portland to St. Maarten
Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Portland with our price prediction graph.
PWM-SXM
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 St. Maarten
PWM-SX0
PWM-SXM
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing St. Maarten
Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated August 23, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Portland to St. Maarten to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Portland to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Portland and St. Maarten flights
Browse other Portland and St. Maarten flight options. Last updated on August 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Portland to St. Maarten
Discover the top 2 airlines that operate flights from Portland to St. Maarten. 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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$305 | Average$561 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$583 | Average$621 | FlexibilityNo cancel fee | On-time71% |