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$160+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$362
(Mytrip)

One-way from

$160
(Trip.com)
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 May 1, 2025.

This Mytrip deal was found by Cheapflights users on 4/30. 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.
Wed 5/211:33 amSJU - PDX
2 stops42h 12mMultiple Airlines
Mon 5/264:35 pmPDX - SJU
3 stops39h 56mMultiple Airlines
Deal found 4/30$362
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Wed 5/211:33 amSJU - PDX
2 stops42h 12mSpirit Airlines
Mon 5/261:37 pmPDX - SJU
2 stops20h 07mSpirit Airlines
Deal found 4/30$369
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/281:12 pmSJU - PDX
2 stops13h 31mDelta
Sun 6/17:14 amPDX - SJU
1 stop13h 28mDelta
Deal found 4/30$379
This JetBlue deal was found by Cheapflights users on 5/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1712:35 pmSJU - PDX
1 stop12h 35mJetBlue
Mon 7/2111:35 pmPDX - SJU
1 stop14h 05mJetBlue
Deal found 5/1$422
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/226:10 amSJU - PDX
1 stop19h 57mAmerican Airlines
Mon 5/2610:24 pmPDX - SJU
1 stop13h 16mAmerican Airlines
Deal found 4/30$451
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/143:23 pmPUJ - PDX
2 stops22h 54mSpirit Airlines
Sat 6/2112:12 pmPDX - PUJ
2 stops22h 58mSpirit Airlines
Deal found 4/30$465
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:05 amSJU - PDX
2 stops14h 58mUnited Airlines
Fri 10/310:14 pmPDX - SJU
1 stop12h 31mUnited Airlines
Deal found 4/30$469
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/132:40 pmMBJ - PDX
2 stops34h 13mUnited Airlines
Fri 5/236:43 pmPDX - MBJ
1 stop19h 02mUnited Airlines
Deal found 4/30$537
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/219:09 pmPUJ - PDX
2 stops17h 08mFrontier
Sun 7/276:16 pmPDX - PUJ
2 stops12h 57mFrontier
Deal found 4/30$562
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/115:54 pmPUJ - PDX
1 stop18h 31mMultiple Airlines
Sat 6/146:39 pmPDX - PUJ
2 stops13h 35mMultiple Airlines
Deal found 4/30$583
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1310:53 amMBJ - PDX
1 stop13h 46mAmerican Airlines
Fri 5/233:24 pmPDX - MBJ
1 stop19h 36mAmerican Airlines
Deal found 4/30$588
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:39 pmKIN - PDX
2 stops22h 18mSpirit Airlines
Thu 5/81:37 pmPDX - KIN
2 stops20h 52mSpirit Airlines
Deal found 4/30$606

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 May 1, 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

Wed 5/21

1:33 am-4:45 pm

2 stops42h 12m

Portland

Mon 5/26

4:35 pm-11:31 am

3 stops39h 56m

$362

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/21

1:33 am-4:45 pm

2 stops42h 12m

Portland

Mon 5/26

1:37 pm-12:44 pm

2 stops20h 07m

$369

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/28

1:12 pm-11:43 pm

2 stops13h 31m

Portland

Sun 6/1

7:14 am-11:42 pm

1 stop13h 28m

$379

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 7/17

12:35 pm-10:10 pm

1 stop12h 35m

Portland

Mon 7/21

11:35 pm-4:40 pm

1 stop14h 05m

$422

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 5/22

6:10 am-11:07 pm

1 stop19h 57m

Portland

Mon 5/26

10:24 pm-2:40 pm

1 stop13h 16m

$451

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Sat 6/14

3:23 pm-11:17 am

2 stops22h 54m

Portland

Sat 6/21

12:12 pm-2:10 pm

2 stops22h 58m

$465

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 9/19

1:05 am-1:03 pm

2 stops14h 58m

Portland

Fri 10/3

10:14 pm-1:45 pm

1 stop12h 31m

$469

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Tue 5/13

2:40 pm-10:53 pm

2 stops34h 13m

Portland

Fri 5/23

6:43 pm-3:45 pm

1 stop19h 02m

$537

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Mon 7/21

9:09 pm-11:17 am

2 stops17h 08m

Portland

Sun 7/27

6:16 pm-10:13 am

2 stops12h 57m

$562

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Wed 6/11

5:54 pm-9:25 am

1 stop18h 31m

Portland

Sat 6/14

6:39 pm-11:14 am

2 stops13h 35m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 58 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 $368). 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 May 1, 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 May 1, 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
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
LATAM Airlines
7.5
Good
1,767 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Frontier, with whom users have recently found tickets for as low as $160. However, be on the lookout for offers from Delta and Spirit Airlines, 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, Santo Domingo Las Americas - Portland or Montego Bay Sangster Intl - 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 $368). 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
Beaverton
Lincoln City
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 Islands to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Caribbean Islands to Portland

Discover the top 5 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$487FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$585FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$342Average$610FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$587FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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