PDX - SXM

$700 Find Cheap Flights from Portland to Simpson Bay - Compare and Save

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 7/14. 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
1 adult, Economy, 0 bags

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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Everything you should know

Cheapest round-trip
$700
Typical prices: $1,099-$866
United Airlines
Tue 7/14Tue 7/21
PDX - SXM • 2 stops
Top airlines
Cheapest • from $700 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $873 (round-trip)
Shortest trip • 10h 36m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Simpson Bay (PDX-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, Jul 14 - Tue, Jul 21
United Airlines Logo
4:15 pm - 12:33 pm
PDX
-
SXM
17h 18m
2 stops
United Airlines Logo
3:50 pm - 9:47 am
SXM
-
PDX
20h 57m
2 stops
$700United Airlines
Sat, Aug 29 - Sun, Sep 6
Delta Logo
5:54 pm - 1:53 pm
PDX
-
SXM
16h 59m
2 stops
Delta Logo
3:18 pm - 8:37 am
SXM
-
PDX
20h 19m
2 stops
$704Delta
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
9:47 pm - 1:51 pm
PDX
-
SXM
13h 04m
1 stop
American Airlines Logo
2:51 pm - 11:55 pm
SXM
-
PDX
12h 04m
1 stop
$759American Airlines
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
7:00 am - 12:33 pm
PDX
-
SXM
26h 33m
2 stops
United Airlines Logo
3:50 pm - 12:07 pm
SXM
-
PDX
23h 17m
3 stops
$820United Airlines
Wed, Jul 29 - Sat, Aug 8
American Airlines Logo
9:47 pm - 1:51 pm
PDX
-
SXM
13h 04m
1 stop
American Airlines Logo
4:39 pm - 11:34 am
SXM
-
PDX
21h 55m
2 stops
$833American Airlines
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
5:15 am - 12:33 pm
PDX
-
SXM
28h 18m
3 stops
United Airlines Logo
3:50 pm - 12:07 pm
SXM
-
PDX
23h 17m
3 stops
$855United Airlines
Wed, Jul 29 - Sat, Aug 8
United Airlines Logo
10:52 pm - 2:43 pm
PDX
-
SXM
12h 51m
1 stop
United Airlines Logo
3:50 pm - 9:34 am
SXM
-
PDX
20h 44m
2 stops
$880United Airlines
Wed, Jul 29 - Sat, Aug 8
United Airlines Logo
1:14 pm - 12:33 pm
PDX
-
SXM
20h 19m
2 stops
United Airlines Logo
3:50 pm - 12:14 pm
SXM
-
PDX
23h 24m
3 stops
$933United Airlines
Wed, Jul 29 - Sat, Aug 8
United Airlines Logo
10:52 pm - 2:43 pm
PDX
-
SXM
12h 51m
1 stop
United Airlines Logo
3:50 pm - 8:19 pm
SXM
-
PDX
31h 29m
1 stop
$1,046United Airlines
Wed, Jul 29 - Sat, Aug 8
American Airlines Logo
9:47 pm - 1:51 pm
PDX
-
SXM
13h 04m
1 stop
American Airlines Logo
1:45 pm - 11:50 am
SXM
-
PDX
25h 05m
1 stop
$3,184American Airlines
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.

How much is a round-trip flight from Portland to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Simpson Bay departing in July.

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 August, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,026 and $1,014 respectively.

Good to know

Low seasonApril
Cheapest flight$700
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

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 5 days, the lowest price for a flight from Portland to Simpson Bay was $700 for a round-trip ticket.

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

    Yes

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

    Portland and Simpson Bay are both served by 1 main airport. You will leave Portland from Portland and will be arriving at 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 is the only airline alliance operating flights between Portland and Simpson Bay.

  • 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 airline flying 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.
7.1
American AirlinesOverall score based on 11668 reviews
7.5Boarding
6.8Entertainment
6.4Food
7.2Comfort
7.9Crew
Airline reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

2.0 MediocreUzair, Jun 2026
SFO - JFK
Read more American Airlines reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

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

Information on your arrival and departure airports