PWM - SXM

$542 Find Cheap Flights from Portland to Simpson Bay

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 1/6. 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

KAYAK searches 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
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Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Simpson Bay

Tue, Jan 6 - Tue, Jan 27
American Airlines Logo
4:50 pm - 3:20 pmPWM-SXM
21h 30m2 stops
American Airlines Logo
5:20 pm - 12:05 pmSXM-PWM
19h 45m2 stops
$542American Airlines
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Tue, Aug 19 - Tue, Aug 26
JetBlue Logo
6:10 am - 1:31 pmPWM-SXM
7h 21m1 stop
JetBlue Logo
2:36 pm - 12:17 amSXM-PWM
9h 41m1 stop
$557JetBlue
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Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
5:10 pm - 1:19 pmPWM-SXM
20h 09m2 stops
American Airlines Logo
4:24 pm - 1:52 pmSXM-PWM
21h 28m2 stops
$567American Airlines
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Tue, Jan 6 - Tue, Jan 27
American Airlines Logo
4:50 pm - 2:05 pmPWM-SXM
20h 15m2 stops
American Airlines Logo
3:25 pm - 10:31 pmSXM-PWM
8h 06m1 stop
$580American Airlines
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Sat, Sep 27 - Wed, Oct 1
Delta Logo
6:33 pm - 1:50 pmPWM-SXM
19h 17m2 stops
Delta Logo
3:20 pm - 2:01 pmSXM-PWM
22h 41m2 stops
$605Delta
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Sat, Sep 27 - Wed, Oct 1
Delta Logo
6:33 pm - 1:50 pmPWM-SXM
19h 17m2 stops
Delta Logo
3:20 pm - 12:11 amSXM-PWM
8h 51m1 stop
$657Delta
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Sat, Oct 4 - Sat, Oct 11
 Logo
6:18 pm - 2:00 pmPWM-SXM
43h 42m3 stops
 Logo
3:05 pm - 2:30 pmSXM-PWM
23h 25m3 stops
Wed, Jan 7 - Sun, Jan 11
United Airlines Logo
7:22 pm - 1:51 pmPWM-SXM
17h 29m2 stops
United Airlines Logo
4:55 pm - 11:17 pmSXM-PWM
31h 22m3 stops
$849United Airlines
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Wed, Jan 7 - Sun, Jan 11
United Airlines Logo
6:00 am - 1:51 pmPWM-SXM
6h 51m1 stop
United Airlines Logo
4:55 pm - 10:44 amSXM-PWM
18h 49m1 stop
$857United Airlines
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Sat, Oct 4 - Sat, Oct 11
 Logo
11:16 am - 1:14 pmPWM-SXM
25h 58m2 stops
 Logo
3:05 pm - 2:30 pmSXM-PWM
23h 25m3 stops
$1,153
Find Deal
Booking Insights

KAYAK's insights & trends for Portland to Simpson Bay flights

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 to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland 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 to Simpson Bay is September, where tickets cost $416 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $1,212 and $1,044 respectively.

Good to know

Low seasonAugust
Cheapest flight$542
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 21% lower on average.
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 to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Portland to Simpson Bay was $542 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?

    oneworld, SkyTeam, 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 $668 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 $811 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.

Reviews of the 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 7980 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Everything you need to know for your flight from Portland to Simpson Bay

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