$589+ Cheap flights from Oregon to Simpson Bay (SXM)
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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SXM
Aug 7 — Aug 141
1 adult, Economy
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1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oregon to Simpson Bay
Keep the following information in mind while searching for Oregon to Simpson Bay flight deals. Data was last updated August 2, 2025.
Round-trip from | $589 (Mytrip) |
|---|---|
Popular in | December |
Cheapest in | January |
Average price | $712 |
Find flight deals from Oregon to Simpson Bay
Cheapest flights from Oregon to Simpson BayExplore the most affordable flight options available from Oregon to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2025.
Explore the most affordable flight options available from Oregon to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2025.
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:07 pmPDX - SXM
3 stops22h 53mSpirit Airlines
Sat 10/113:05 pmSXM - PDX
3 stops30h 59mSpirit Airlines
Deal found 8/1![Spirit Airlines logo]()
$589
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:00 pmPDX - SXM
2 stops41h 00mAir Canada
Mon 12/155:00 pmSXM - PDX
2 stops29h 30mAir Canada
Deal found 8/1![Air Canada logo]()
$666
This American Airlines deal was found by Cheapflights users on 8/1. 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 9/1612:04 pmPDX - SXM
2 stops22h 15mAmerican Airlines
Tue 9/232:20 pmSXM - PDX
2 stops22h 27mAmerican Airlines
Deal found 8/1![American Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Fri 10/2410:17 pmPDX - SXM
1 stop11h 12mUnited Airlines
Fri 10/311:52 pmSXM - PDX
2 stops22h 46mUnited Airlines
Deal found 8/1![United Airlines logo]()
$717
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:05 pmPDX - SXM
1 stop12h 45mDelta
Fri 10/103:14 pmSXM - PDX
2 stops24h 27mDelta
Deal found 8/1![Delta logo]()
$750
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/43:27 pmPDX - SXM
3 stops43h 33mMultiple Airlines
Fri 8/83:05 pmSXM - PDX
3 stops26h 10mMultiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$1,042
This WestJet deal was found by Cheapflights users on 8/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:55 amPDX - SXM
2 stops34h 26mWestJet
Mon 12/154:20 pmSXM - PDX
2 stops24h 43mWestJet
Deal found 8/1![WestJet logo]()
$3,712
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Simpson Bay 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 2,558,603 searches. Data last updated August 2, 2025.
Use the filters below to find and compare flights from Oregon to Simpson Bay that are best for you.
Fly from
Oregon
Fly to
Simpson Bay
Route
Depart
Return
Price
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Fri 10/3
12:07 pm-2:00 pm
3 stops22h 53m
Simpson Bay Princess Juliana
Sat 10/11
3:05 pm-7:04 pm
3 stops30h 59m
$589
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Sat 12/6
7:00 pm-4:00 pm
2 stops41h 00m
Simpson Bay Princess Juliana
Mon 12/15
5:00 pm-6:30 pm
2 stops29h 30m
$666
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Tue 9/16
12:04 pm-1:19 pm
2 stops22h 15m
Simpson Bay Princess Juliana
Tue 9/23
2:20 pm-9:47 am
2 stops22h 27m
$692
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Fri 10/24
10:17 pm-12:29 pm
1 stop11h 12m
Simpson Bay Princess Juliana
Fri 10/31
1:52 pm-9:38 am
2 stops22h 46m
$717
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Fri 10/3
10:05 pm-1:50 pm
1 stop12h 45m
Simpson Bay Princess Juliana
Fri 10/10
3:14 pm-12:41 pm
2 stops24h 27m
$750
PortlandSimpson Bay
PDX - SXM
PDXSXM
Portland
Fri 12/5
12:55 am-3:21 pm
2 stops34h 26m
Simpson Bay Princess Juliana
Mon 12/15
4:20 pm-1:03 pm
2 stops24h 43m
$3,712
Best time to book a flight from Oregon to Simpson Bay
Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Oregon with our price prediction graph.
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 Oregon to Simpson Bay
What is the cheapest month to book a flight from Oregon to Simpson Bay?
Currently, September is the cheapest month in which you can book a flight from Oregon to Simpson Bay (average of $459). Flying from Oregon to Simpson Bay in March is currently the most expensive (average of $655). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from OR to SXM?
Find hourly flight availability from Oregon to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Simpson Bay as you normally would.
How much does it cost to fly round-trip from Oregon to Simpson Bay?
Reviews of airlines servicing Simpson Bay
Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated August 2, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Oregon to Simpson Bay. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Entertainment
7.9
Boarding
8.2
Crew
8.5
Food
7.3
Comfort
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Oregon to Simpson Bay. 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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Alternative routes for Oregon to Simpson Bay
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Oregon to Simpson Bay
Discover the top 2 airlines that operate flights from Oregon to Simpson Bay. 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 2,558,603 searches. Data last updated August 2, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$515 | Average$901 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$602 | Average$849 | FlexibilityNo cancel fee | On-time71% |