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$150+ Cheap flights from Caribbean Islands 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Portland

Keep the following information in mind while searching for Caribbean Islands to Portland flight deals. Data was last updated April 4, 2025.

Round-trip from

$365
(Mytrip)

One-way from

$150
(Mytrip)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
Search Deals

Find flight deals from Caribbean Islands to Portland

Cheapest flights from Caribbean Islands to Portland
Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2025.

This Mytrip deal was found by Cheapflights users on 4/3. 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.
Thu 5/112:54 amSJU - PDX
2 stops39h 43mSpirit Airlines
Tue 5/67:01 pmPDX - SJU
3 stops24h 37mSpirit Airlines
Deal found 4/3$365
This Delta deal was found by Cheapflights users on 4/4. 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 5/71:12 pmSJU - PDX
1 stop13h 03mDelta
Mon 5/1211:11 pmPDX - SJU
1 stop10h 34mDelta
Deal found 4/4$369
This American Airlines deal was found by Cheapflights users on 4/4. 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 4/262:35 pmSJU - PDX
1 stop11h 27mAmerican Airlines
Sat 5/37:35 amPDX - SJU
1 stop18h 25mAmerican Airlines
Deal found 4/4$378
This United Airlines deal was found by Cheapflights users on 4/4. 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 stops16h 49mUnited Airlines
Mon 5/126:30 pmPDX - SJU
2 stops15h 04mUnited Airlines
Deal found 4/4$459
This Mytrip deal was found by Cheapflights users on 4/4. 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 5/191:34 pmKIN - PDX
2 stops25h 08mMultiple Airlines
Mon 5/264:35 pmPDX - KIN
2 stops17h 54mMultiple Airlines
Deal found 4/4$494
This Mytrip deal was found by Cheapflights users on 4/3. 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
3 stops38h 09mMultiple Airlines
Mon 5/269:11 amPDX - SJU
2 stops26h 49mMultiple Airlines
Deal found 4/3$510
This Southwest deal was found by Cheapflights users on 4/4. 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.
Thu 6/125:30 amSJU - PDX
1 stop13h 15mSouthwest
Mon 6/236:55 pmPDX - SJU
2 stops12h 45mSouthwest
Deal found 4/4$520
This United Airlines deal was found by Cheapflights users on 4/4. 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.
Mon 5/512:15 amBQN - PDX
2 stops15h 24mUnited Airlines
Mon 5/1211:59 pmPDX - BQN
2 stops20h 10mUnited Airlines
Deal found 4/4$567
This American Airlines deal was found by Cheapflights users on 4/4. 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 5/192:30 pmKIN - PDX
1 stop10h 37mAmerican Airlines
Mon 5/2610:24 pmPDX - KIN
1 stop13h 01mAmerican Airlines
Deal found 4/4$571
This Mytrip deal was found by Cheapflights users on 4/4. 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 5/191:34 pmKIN - PDX
3 stops29h 11mSpirit Airlines
Mon 5/265:40 pmPDX - KIN
3 stops40h 49mSpirit Airlines
Deal found 4/4$614
This Mytrip deal was found by Cheapflights users on 4/4. 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 5/1912:07 pmMBJ - PDX
2 stops30h 38mSpirit Airlines
Mon 5/265:40 pmPDX - MBJ
3 stops39h 22mSpirit Airlines
Deal found 4/4$614
This Mytrip deal was found by Cheapflights users on 4/4. 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 5/1912:07 pmMBJ - PDX
2 stops26h 35mMultiple Airlines
Mon 5/268:08 amPDX - MBJ
2 stops24h 54mMultiple Airlines
Deal found 4/4$617

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands 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 4, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Portland that are best for you.

Fly from

Caribbean Islands

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 5/1

12:54 am-1:37 pm

2 stops39h 43m

Portland

Tue 5/6

7:01 pm-10:38 pm

3 stops24h 37m

$365

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/7

1:12 pm-11:15 pm

1 stop13h 03m

Portland

Mon 5/12

11:11 pm-12:45 pm

1 stop10h 34m

$369

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 4/26

2:35 pm-11:02 pm

1 stop11h 27m

Portland

Sat 5/3

7:35 am-5:00 am

1 stop18h 25m

$378

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-2:54 pm

2 stops16h 49m

Portland

Mon 5/12

6:30 pm-12:34 pm

2 stops15h 04m

$459

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 5/19

1:34 pm-12:42 pm

2 stops25h 08m

Portland

Mon 5/26

4:35 pm-12:29 pm

2 stops17h 54m

$494

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/21

1:33 am-12:42 pm

3 stops38h 09m

Portland

Mon 5/26

9:11 am-3:00 pm

2 stops26h 49m

$510

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 6/12

5:30 am-3:45 pm

1 stop13h 15m

Portland

Mon 6/23

6:55 pm-10:40 am

2 stops12h 45m

$520

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

Mon 5/5

12:15 am-12:39 pm

2 stops15h 24m

Portland

Mon 5/12

11:59 pm-11:09 pm

2 stops20h 10m

$567

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 5/19

2:30 pm-11:07 pm

1 stop10h 37m

Portland

Mon 5/26

10:24 pm-1:25 pm

1 stop13h 01m

$571

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 5/19

1:34 pm-4:45 pm

3 stops29h 11m

Portland

Mon 5/26

5:40 pm-12:29 pm

3 stops40h 49m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 50 results
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Best time to book a flight from Caribbean Islands to Portland

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $277). Flying from Caribbean Islands 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 EPX to PDX?

Find hourly flight availability from Caribbean Islands 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 4, 2025.

When flying from Caribbean Islands 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 4, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Caribbean Islands to Portland have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,837 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
LATAM Airlines
7.5
Good
1,753 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean Islands 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 Islands to Portland one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $150. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Caribbean Islands to Portland for a low price.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Portland, Punta Cana - Portland or Santo Domingo Las Americas - Portland when deciding on the best route from Caribbean Islands to Portland.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Islands to Portland?

    Currently, November is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $277). Flying from Caribbean Islands 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 Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Lincoln City
Beaverton
Seaside
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Long Beach
Cannon Beach
Tigard
Astoria
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 Islands 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 Islands to Portland

Discover the top 6 airlines that operate flights from Caribbean Islands 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$310Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$312Average$597FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$342Average$559FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$435FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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