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$118+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Round-trip from

$289
(Mytrip)

One-way from

$118
(Trip.com)

Popular in

November

Cheapest in

February

Average price

$454
From Caribbean to Portland
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One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($55 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 January 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 January 30, 2025.

This Mytrip deal was found by Cheapflights users on 1/30. 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.
Fri 2/142:25 pmSJU - PDX
2 stops22h 56mSpirit Airlines
Tue 2/1810:16 amPDX - SJU
2 stops26h 45mSpirit Airlines
Deal found 1/30$289
This Southwest deal was found by Cheapflights users on 1/29. 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.
Fri 9/55:50 amSJU - PDX
1 stop13h 00mSouthwest
Wed 9/106:10 amPDX - SJU
2 stops13h 20mSouthwest
Deal found 1/29$392
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Sat 9/201:55 pmSJU - PDX
1 stop12h 05mAmerican Airlines
Fri 10/311:10 pmPDX - SJU
1 stop18h 00mAmerican Airlines
Deal found 1/30$422
This United Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 9/41:05 amSJU - PDX
1 stop13h 54mUnited Airlines
Wed 9/107:10 amPDX - SJU
1 stop10h 28mUnited Airlines
Deal found 1/29$449
This Delta deal was found by Cheapflights users on 1/30. 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.
Sat 9/202:15 pmSJU - PDX
2 stops12h 37mDelta
Fri 10/310:55 pmPDX - SJU
1 stop11h 15mDelta
Deal found 1/30$465
This FlightHub deal was found by Cheapflights users on 1/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/141:36 pmKIN - PDX
2 stops20h 46mSpirit Airlines
Sat 5/37:03 pmPDX - KIN
2 stops15h 28mSpirit Airlines
Deal found 1/30$515
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Mon 4/144:12 pmMBJ - PDX
2 stops28h 33mUnited Airlines
Sat 5/36:30 pmPDX - MBJ
2 stops16h 40mUnited Airlines
Deal found 1/30$594
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 3/49:00 amKIN - PDX
2 stops14h 42mDelta
Tue 4/156:04 amPDX - KIN
1 stop12h 05mDelta
Deal found 1/30$616
This American Airlines deal was found by Cheapflights users on 1/30. 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 3/42:57 pmKIN - PDX
1 stop12h 01mAmerican Airlines
Tue 4/1510:34 pmPDX - KIN
1 stop19h 06mAmerican Airlines
Deal found 1/30$625
This eDestinos deal was found by Cheapflights users on 1/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/106:00 amSJU - PDX
2 stops53h 47mFrontier
Sat 4/196:40 amPDX - SJU
2 stops30h 17mFrontier
Deal found 1/30$634
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Mon 4/142:25 pmMBJ - PDX
1 stop10h 31mAmerican Airlines
Sat 5/311:46 pmPDX - MBJ
1 stop11h 29mAmerican Airlines
Deal found 1/30$670
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Mon 4/142:57 pmKIN - PDX
2 stops48h 04mUnited Airlines
Sat 5/31:45 pmPDX - KIN
3 stops46h 08mUnited Airlines
Deal found 1/30$958

Find flights from Caribbean to Portland within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 2/14

2:25 pm-9:21 am

2 stops22h 56m

Portland

Tue 2/18

10:16 am-5:01 pm

2 stops26h 45m

$289

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/10

6:15 am-6:02 pm

1 stop14h 47m

Portland

Fri 4/18

12:40 am-2:21 pm

1 stop10h 41m

$475

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/10

1:29 pm-11:13 pm

1 stop12h 44m

Portland

Sat 4/19

11:46 pm-1:45 pm

1 stop10h 59m

$494

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 4/14

1:36 pm-8:22 am

2 stops20h 46m

Portland

Sat 5/3

7:03 pm-12:31 pm

2 stops15h 28m

$515

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Mon 4/14

4:12 pm-6:45 pm

2 stops28h 33m

Portland

Sat 5/3

6:30 pm-1:10 pm

2 stops16h 40m

$594

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Tue 3/4

9:00 am-8:42 pm

2 stops14h 42m

Portland

Tue 4/15

6:04 am-8:09 pm

1 stop12h 05m

$616

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Tue 3/4

2:57 pm-11:58 pm

1 stop12h 01m

Portland

Tue 4/15

10:34 pm-7:40 pm

1 stop19h 06m

$625

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 4/25

1:05 am-6:33 pm

2 stops20h 28m

Portland

Sat 5/3

11:59 pm-2:44 pm

1 stop11h 45m

$631

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/10

6:00 am-8:47 am

2 stops53h 47m

Portland

Sat 4/19

6:40 am-3:57 pm

2 stops30h 17m

$634

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Mon 4/14

2:25 pm-10:56 pm

1 stop10h 31m

Portland

Sat 5/3

11:46 pm-1:15 pm

1 stop11h 29m

$670

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 30 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.

Travel insights for flights from Caribbean to Portland

Get recent, data-driven insights about flights from Caribbean to Portland including ideal travel times, pricing trends, and more.

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 $376). 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 January 30, 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 January 30, 2025.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,156 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $118 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $128 and American Airlines from $180 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, Santo Domingo Las Americas - Portland or Montego Bay Sangster Intl - 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 $376). 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
Seaside
Lincoln City
Beaverton
McMinnville
Lake Oswego
Vancouver
Hillsboro
Gresham
Long Beach
Cannon Beach
Tigard
Hood River
Astoria
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Wilsonville
Silverton

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 5 airlines flying from Caribbean to Portland

Discover the top 5 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$308Average$597FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$340Average$478FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$564FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$443FlexibilityNo cancel feeOn-timeN/A
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