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PWM - SXM

Find cheap flights from Portland to Simpson Bay from $444

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 Simpson Bay departing on 9/14. 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
0 bags
Sat 6/8
Sat 6/15

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Simpson Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

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Cheap flight deals from Portland to Simpson Bay (PWM-SXM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Simpson Bay 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 and deals for you by selecting your travel dates.
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6:05 am - 1:49 pmPWM-SXM
7h 44m1 stop
3:19 pm - 9:33 amSXM-PWM
18h 14m2 stops
$444Delta
Find Deal
Sat, Sep 14 - Wed, Sep 18
5:31 am - 1:40 pmPWM-SXM
32h 09m2 stops
3:20 pm - 9:58 pmSXM-PWM
30h 38m1 stop
$599Delta
Find Deal
Mon, May 27 - Wed, Jun 12
2:51 pm - 1:40 pmPWM-SXM
22h 49m2 stops
3:20 pm - 10:45 amSXM-PWM
19h 25m2 stops
$623Delta
Find Deal
Mon, May 27 - Thu, Jun 13
1:25 pm - 1:40 pmPWM-SXM
48h 15m2 stops
3:20 pm - 4:12 pmSXM-PWM
24h 52m2 stops
$649Delta
Find Deal
Sat, May 25 - Thu, Jun 13
7:45 am - 12:57 pmPWM-SXM
29h 12m1 stop
2:35 pm - 11:48 amSXM-PWM
21h 13m2 stops
$686American Airlines
Find Deal
Sat, May 25 - Fri, May 31
2:32 pm - 12:35 pmPWM-SXM
22h 03m1 stop
1:30 pm - 11:58 pmSXM-PWM
34h 28m2 stops
$714United Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
12:21 pm - 12:57 pmPWM-SXM
24h 36m1 stop
4:15 pm - 12:52 amSXM-PWM
8h 37m1 stop
$719American Airlines
Find Deal
Sun, May 26 - Sat, Jun 15
12:21 pm - 12:57 pmPWM-SXM
24h 36m1 stop
12:50 pm - 10:22 amSXM-PWM
21h 32m2 stops
$724American Airlines
Find Deal
Sun, May 26 - Sat, Jun 15
12:35 pm - 12:57 pmPWM-SXM
24h 22m2 stops
4:05 pm - 1:59 pmSXM-PWM
21h 54m2 stops
$742American Airlines
Find Deal
Sun, May 26 - Wed, May 29
3:41 pm - 12:57 pmPWM-SXM
21h 16m2 stops
12:35 pm - 11:47 pmSXM-PWM
11h 12m2 stops
$791American Airlines
Find Deal
Sat, May 25 - Wed, May 29

Flights from Portland to Simpson Bay - Travel Insights & Trends

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Portland, Maine to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Portland, Maine to Simpson Bay is September, where tickets cost $511 on average. On the other hand, the most expensive months are March and July, where the average cost of tickets is $1,262 and $1,121 respectively.

Good to know

Low season

May

High season

March

Cheapest flight

$444
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 56% increase in price.
Flight from Portland to Simpson Bay

When to book flights from Portland to Simpson Bay

Are your dates flexible? Find out the best times to travel from Portland to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to Simpson Bay

  • What is the cheapest flight from Portland, Maine to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Portland, Maine to Simpson Bay was $444 for a round-trip ticket.

  • Do I need a passport to fly between Portland and Simpson Bay?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Portland and on arrival in Simpson Bay.

  • Which airports will I be using when flying from Portland to Simpson Bay?

    When flying out of Portland you will be using Portland. You will be landing at Simpson Bay, also known as Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Portland to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Simpson Bay?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Portland and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Portland to Simpson Bay, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Simpson Bay are Delta and United Airlines. With an average price for the route of $767 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $848 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Portland to Simpson Bay?

    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 Simpson Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Portland 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 Simpson Bay?

    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 to Simpson Bay with an airline and back to Portland with another airline. Booking your flights between Portland and SXM can sometimes prove cheaper using this method.

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

    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 to Simpson Bay from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Portland to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Portland to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Simpson Bay? 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.
8.0
DeltaOverall score based on 10778 reviews
8.2Boarding
7.4Food
8.6Crew
7.9Comfort
8.0Entertainment
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Portland - Simpson Bay Flights

Departure:

Portland (undefined)United States

Destination:

Simpson Bay (SXM)St. Maarten

Cabin classes: