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$161+ Cheap flights from Caribbean to Portland (PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated April 11, 2025.

Round-trip from

$317
(Mytrip)

One-way from

$161
(Mytrip)

Popular in

November

Cheapest in

February

Average price

$523
From Caribbean to Portland
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One-way flight from Caribbean to Portland
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Highest demand for flights based on searches. 11% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

This Mytrip deal was found by Cheapflights users on 4/8. 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.
Wed 4/2312:54 amSJU - PDX
2 stops35h 18mSpirit Airlines
Mon 4/287:01 pmPDX - SJU
2 stops21h 39mSpirit Airlines
Deal found 4/8$317
This Delta deal was found by Cheapflights users on 4/9. 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.
Wed 5/71:55 pmSJU - PDX
1 stop11h 06mDelta
Mon 5/127:14 amPDX - SJU
1 stop13h 28mDelta
Deal found 4/9$369
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Sat 4/266:05 amSJU - PDX
1 stop15h 38mAmerican Airlines
Sat 5/311:57 amPDX - SJU
1 stop14h 03mAmerican Airlines
Deal found 4/10$440
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Tue 5/61:05 amSJU - PDX
2 stops17h 10mUnited Airlines
Mon 5/126:30 pmPDX - SJU
2 stops16h 15mUnited Airlines
Deal found 4/9$459
This Mytrip deal was found by Cheapflights users on 4/9. 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.
Wed 5/211:33 amSJU - PDX
2 stops41h 17mMultiple Airlines
Tue 5/271:37 pmPDX - SJU
2 stops18h 54mMultiple Airlines
Deal found 4/9$468
This JetBlue deal was found by Cheapflights users on 4/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2412:35 pmSJU - PDX
1 stop12h 35mJetBlue
Sat 6/2811:35 pmPDX - SJU
1 stop10h 30mJetBlue
Deal found 4/8$508
This Southwest deal was found by Cheapflights users on 4/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/95:30 amSJU - PDX
1 stop13h 15mSouthwest
Mon 6/166:55 pmPDX - SJU
2 stops12h 45mSouthwest
Deal found 4/9$539
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Wed 6/186:25 pmKIN - PDX
2 stops20h 27mMultiple Airlines
Sun 6/291:45 pmPDX - KIN
3 stops25h 25mMultiple Airlines
Deal found 4/10$563
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/512:59 amSJU - PDX
2 stops25h 39mAlaska Airlines
Sun 8/1010:52 pmPDX - SJU
1 stop12h 26mAlaska Airlines
Deal found 4/9$684
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Mon 6/166:00 amKIN - PDX
2 stops16h 48mAmerican Airlines
Sat 6/2812:07 amPDX - KIN
2 stops17h 48mAmerican Airlines
Deal found 4/10$690
This Travelocity deal was found by Cheapflights users on 4/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/171:34 pmKIN - PDX
2 stops24h 13mSpirit Airlines
Sun 6/2912:42 pmPDX - KIN
2 stops21h 46mSpirit Airlines
Deal found 4/10$694
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Tue 5/273:20 pmSDQ - PDX
2 stops23h 36mUnited Airlines
Thu 6/121:25 pmPDX - SDQ
2 stops21h 45mUnited Airlines
Deal found 4/9$702

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean to Portland 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 April 11, 2025.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 4/23

12:54 am-9:12 am

2 stops35h 18m

Portland

Mon 4/28

7:01 pm-7:40 pm

2 stops21h 39m

$317

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/7

1:55 pm-10:01 pm

1 stop11h 06m

Portland

Mon 5/12

7:14 am-11:42 pm

1 stop13h 28m

$369

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 4/26

6:05 am-6:43 pm

1 stop15h 38m

Portland

Sat 5/3

11:57 am-5:00 am

1 stop14h 03m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-3:15 pm

2 stops17h 10m

Portland

Mon 5/12

6:30 pm-1:45 pm

2 stops16h 15m

$459

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/21

1:33 am-3:50 pm

2 stops41h 17m

Portland

Tue 5/27

1:37 pm-11:31 am

2 stops18h 54m

$468

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 6/24

12:35 pm-10:10 pm

1 stop12h 35m

Portland

Sat 6/28

11:35 pm-1:05 pm

1 stop10h 30m

$508

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 6/9

5:30 am-3:45 pm

1 stop13h 15m

Portland

Mon 6/16

6:55 pm-10:40 am

2 stops12h 45m

$539

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Wed 6/18

6:25 pm-12:52 pm

2 stops20h 27m

Portland

Sun 6/29

1:45 pm-5:10 pm

3 stops25h 25m

$563

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 6/5

12:59 am-11:38 pm

2 stops25h 39m

Portland

Sun 8/10

10:52 pm-2:18 pm

1 stop12h 26m

$684

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 6/16

6:00 am-8:48 pm

2 stops16h 48m

Portland

Sat 6/28

12:07 am-7:55 pm

2 stops17h 48m

$690

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 43 results
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Best time to book a flight from Caribbean to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean 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 Caribbean to Portland

What is the cheapest month to book a flight from Caribbean to Portland?

Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $369). 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 CB to PDX?

Find hourly flight availability from Caribbean to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

When flying from Caribbean to Portland, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 11, 2025.
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,851 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,910 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,757 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,636 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Caribbean?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean to Portland. It is only a 6.0 mi journey from Portland (PDX) to Portland’s city center.

  • What are the cheapest airlines to fly from Caribbean to Portland one-way?

    One-way options have recently been found by users for as low as $161 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $185 and American Airlines from $188 one-way.

  • What are the most popular routes from Caribbean to Portland?

    When deciding which route to take from Caribbean to Portland consider San Juan Luis Munoz Marin Intl - Portland, Santiago de los Caballeros - Portland or Kingston Norman Manley - Portland as they are the most popular.

  • Can I find deals for flights from Caribbean to Portland that include hotel bookings?

    Yes. In addition to deals on Caribbean to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Portland.

  • Can I find deals for business class flights from Caribbean to Portland?

    Yes. Cheapflights offers flight deals from Caribbean to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Caribbean to Portland?

    Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $369). 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.

See more FAQs

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Lincoln City
Beaverton
Seaside
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Caribbean to Portland

Discover the top 6 airlines that operate flights from Caribbean to Portland. 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 April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$487FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$310Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$312Average$597FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$342Average$604FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$591FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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