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$186+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$362
(Booking.com)

One-way from

$186
(FlightHub)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
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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 June 16, 2025.

This Booking.com deal was found by Cheapflights users on 6/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3012:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
Wed 8/63:10 pmPDX - MBJ
2 stops16h 43mSpirit Airlines
Deal found 6/15$362
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Tue 7/154:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Tue 7/2210:23 amPDX - SJU
2 stops22h 09mSpirit Airlines
Deal found 6/15$377
This JetBlue deal was found by Cheapflights users on 6/15. 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.
Mon 7/1412:55 pmSJU - PDX
1 stop12h 20mJetBlue
Tue 7/1511:40 pmPDX - SJU
1 stop13h 24mJetBlue
Deal found 6/15$380
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 10/281:10 pmSJU - PDX
1 stop13h 19mDelta
Tue 11/47:00 amPDX - SJU
1 stop12h 34mDelta
Deal found 6/16$399
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 7/118:30 amSJU - PDX
1 stop16h 36mAmerican Airlines
Tue 7/1511:54 pmPDX - SJU
2 stops12h 41mAmerican Airlines
Deal found 6/14$481
This United Airlines deal was found by Cheapflights users on 6/15. 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
1 stop11h 13mUnited Airlines
Wed 9/247:35 pmPDX - SJU
2 stops17h 07mUnited Airlines
Deal found 6/15$489
This Southwest deal was found by Cheapflights users on 6/15. 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 7/145:30 amSJU - PDX
1 stop13h 15mSouthwest
Tue 7/155:40 amPDX - SJU
2 stops12h 35mSouthwest
Deal found 6/15$530
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Sun 6/292:36 amSJU - PDX
2 stops16h 11mMultiple Airlines
Sun 7/1310:23 amPDX - SJU
3 stops32h 14mMultiple Airlines
Deal found 6/15$536
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Sun 9/1412:15 amBQN - PDX
1 stop11h 38mUnited Airlines
Fri 9/199:59 amPDX - BQN
1 stop10h 10mUnited Airlines
Deal found 6/16$542
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/31:37 pmKIN - PDX
2 stops23h 40mSpirit Airlines
Sun 7/612:12 pmPDX - KIN
2 stops22h 20mSpirit Airlines
Deal found 6/14$544
This Southwest deal was found by Cheapflights users on 6/15. 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 6/2612:45 pmMBJ - PDX
2 stops13h 20mSouthwest
Mon 6/309:15 pmPDX - MBJ
1 stop14h 40mSouthwest
Deal found 6/15$625
This Mytrip deal was found by Cheapflights users on 6/14. 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.
Tue 7/297:05 amKIN - PDX
2 stops28h 13mMultiple Airlines
Tue 8/53:10 pmPDX - KIN
2 stops27h 25mMultiple Airlines
Deal found 6/14$629

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 June 16, 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

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Wed 7/30

12:10 pm-9:18 am

2 stops23h 08m

Portland

Wed 8/6

3:10 pm-9:53 am

2 stops16h 43m

$362

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-2:15 pm

2 stops24h 32m

Portland

Tue 7/22

10:23 am-11:32 am

2 stops22h 09m

$377

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 7/14

12:55 pm-10:15 pm

1 stop12h 20m

Portland

Tue 7/15

11:40 pm-4:04 pm

1 stop13h 24m

$380

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 9/5

2:40 pm-10:12 pm

1 stop10h 32m

Portland

Fri 9/12

10:55 pm-1:10 pm

1 stop11h 15m

$399

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 7/11

8:30 am-10:06 pm

1 stop16h 36m

Portland

Tue 7/15

11:07 pm-10:50 pm

1 stop20h 43m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/4

1:05 am-8:53 am

1 stop10h 48m

Portland

Fri 9/12

5:40 pm-12:00 pm

2 stops15h 20m

$489

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sun 6/29

2:36 am-3:47 pm

2 stops16h 11m

Portland

Sun 7/13

10:23 am-9:09 pm

2 stops31h 46m

$521

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 7/14

5:30 am-3:45 pm

1 stop13h 15m

Portland

Tue 7/15

5:40 am-9:15 pm

2 stops12h 35m

$530

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

Sun 9/14

12:15 am-8:53 am

1 stop11h 38m

Portland

Fri 9/19

9:59 am-11:09 pm

1 stop10h 10m

$542

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Thu 7/3

1:37 pm-11:17 am

2 stops23h 40m

Portland

Sun 7/6

12:12 pm-12:32 pm

2 stops22h 20m

$544

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 55 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 June 16, 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 June 16, 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
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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
1,785 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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
8,798 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

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 Spirit Airlines, with whom users have recently found tickets for as low as $186. However, be on the lookout for offers from JetBlue and Southwest, 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, Kingston Norman Manley - Portland or Culebra - 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
Seaside
Vancouver
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Longview
Hood River
Depoe Bay
Woodburn
Stevenson
Pacific City
Troutdale

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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$232Average$394FlexibilityNo cancel feeOn-time62%
DeltaCheapest$290Average$630FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$622FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$597FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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