$790 Find Cheap Flights from Portland to St. Maarten

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to St. Maarten departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Book Cheap Portland to St. Maarten Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to St. Maarten that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to St. Maarten

Sat, May 30 - Sat, Jun 6
American Airlines Logo
9:57 pm - 1:50 pm
PDX
-
SXM
12h 53m
1 stop
American Airlines Logo
12:17 pm - 11:59 pm
SXM
-
PDX
14h 42m
1 stop
$790American Airlines
Sat, May 30 - Sat, Jun 6
American Airlines Logo
5:28 pm - 1:22 pm
PDX
-
SXM
16h 54m
2 stops
American Airlines Logo
2:50 pm - 9:54 am
SXM
-
PDX
22h 04m
2 stops
$795American Airlines
Sat, May 30 - Sat, Jun 6
Multiple Airlines Logo
2:30 pm - 2:20 pm
PDX
-
SXM
20h 50m
3 stops
Multiple Airlines Logo
6:00 pm - 5:39 pm
SXM
-
PDX
26h 39m
2 stops
$815Multiple Airlines
Wed, Jul 29 - Sat, Aug 8
Air Canada Logo
7:45 pm - 5:00 pm
PDX
-
SXM
18h 15m
2 stops
Air Canada Logo
6:00 pm - 9:31 am
SXM
-
PDX
42h 31m
2 stops
$824Air Canada
Wed, Jul 29 - Sat, Aug 8
Air Canada Logo
7:45 pm - 5:00 pm
PDX
-
SXM
18h 15m
2 stops
Air Canada Logo
6:00 pm - 9:31 am
SXM
-
PDX
42h 31m
2 stops
$864Air Canada
Wed, Jul 29 - Sat, Aug 8
American Airlines Logo
9:47 pm - 1:51 pm
PDX
-
SXM
13h 04m
1 stop
American Airlines Logo
2:42 pm - 9:24 am
SXM
-
PDX
21h 42m
2 stops
$865American Airlines
Sat, May 30 - Sat, Jun 6
Multiple Airlines Logo
2:30 pm - 2:20 pm
PDX
-
SXM
20h 50m
3 stops
Multiple Airlines Logo
2:35 pm - 5:39 pm
SXM
-
PDX
30h 04m
3 stops
$880Multiple Airlines
Wed, Apr 29 - Tue, May 12
American Airlines Logo
1:52 pm - 11:37 am
PDX
-
SXM
18h 45m
2 stops
American Airlines Logo
2:21 pm - 11:53 pm
SXM
-
PDX
12h 32m
1 stop
$890American Airlines
Fri, May 22 - Sat, May 30
Multiple Airlines Logo
2:30 pm - 5:00 pm
PDX
-
SXM
23h 30m
2 stops
Multiple Airlines Logo
2:35 pm - 5:26 pm
SXM
-
PDX
29h 51m
3 stops
$903Multiple Airlines
Fri, May 22 - Sat, May 30
United Airlines Logo
11:30 pm - 12:33 pm
PDX
-
SXM
10h 03m
1 stop
United Airlines Logo
3:50 pm - 11:38 am
SXM
-
PDX
22h 48m
2 stops
$917United Airlines
Booking Insights

KAYAK's insights & trends for Portland to St. Maarten flights

Get data-powered insights and trends into flights from Portland to St. Maarten to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Portland to St. Maarten take?

The duration of a flight to St. Maarten depends on your arrival airport. The shortest route to St. Maarten from Portland is to Simpson Bay, which takes 18h 30m.

Good to know

Low seasonMarch
Cheapest flight$790
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Portland to Simpson Bay

FAQs - booking St. Maarten flights

  • How does KAYAK find such low prices on flights from Portland to St. Maarten?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to St. Maarten.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to St. Maarten?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to St. Maarten is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to St. Maarten?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Portland to St. Maarten with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to St. Maarten?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Portland to St. Maarten up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Portland to St. Maarten

 
Need help choosing which airline to fly with from Portland to St. Maarten? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11580 reviews
7.2Comfort
7.5Boarding
6.4Food
6.9Entertainment
7.9Crew
Airline reviews

Flight was fine, but not having WiFi was a major negative

6.0 GoodJosephine, Apr 2026
CHS - LGA
Read more American Airlines reviews

Flight was fine, but not having WiFi was a major negative

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.

Everything you need to know for your flight from Portland to St. Maarten

Information on your arrival and departure airports