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$185+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$367
(Mytrip)

One-way from

$185
(FlightHub)

Popular in

November

Cheapest in

August

Average price

$636
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. 10% potential increase in price ($59 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 June 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 junio 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
mar. 7/154:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
lun. 7/213:10 pmPDX - SJU
3 stops20h 35mSpirit Airlines
Deal found 6/11$367
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/2412:55 pmSJU - PDX
1 stop12h 20mJetBlue
lun. 7/2811:40 pmPDX - SJU
1 stop13h 24mJetBlue
Deal found 6/10$380
This Mytrip deal was found by Cheapflights users on 6/11. 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.
mar. 7/154:43 pmSJU - PDX
2 stops24h 32mMultiple Airlines
lun. 7/219:22 amPDX - SJU
2 stops27h 08mMultiple Airlines
Deal found 6/11$383
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/207:30 amSJU - PDX
2 stops15h 55mDelta
vie. 10/37:14 pmPDX - SJU
2 stops13h 49mDelta
Deal found 6/10$399
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/1012:59 amSJU - PDX
2 stops14h 52mFrontier
lun. 7/146:35 amPDX - SJU
2 stops15h 11mFrontier
Deal found 6/10$433
This American Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 7/193:23 pmSJU - PDX
1 stop21h 28mAmerican Airlines
sáb. 8/1611:07 pmPDX - SJU
1 stop20h 42mAmerican Airlines
Deal found 6/11$440
This FlightHub deal was found by Cheapflights users on 6/11. 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.
sáb. 7/58:53 amKIN - PDX
2 stops28h 24mSpirit Airlines
sáb. 7/123:10 pmPDX - KIN
2 stops17h 50mSpirit Airlines
Deal found 6/11$461
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/143:20 amBQN - PDX
2 stops23h 56mFrontier
vie. 9/1911:36 amPDX - BQN
2 stops20h 15mFrontier
Deal found 6/10$483
This United Airlines deal was found by Cheapflights users on 6/12. 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.
vie. 9/191:05 amSJU - PDX
2 stops14h 58mUnited Airlines
vie. 10/310:17 pmPDX - SJU
1 stop12h 28mUnited Airlines
Deal found 6/12$489
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/3012:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
sáb. 8/93:10 pmPDX - MBJ
2 stops19h 35mSpirit Airlines
Deal found 6/10$493
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/112:40 pmSJU - PDX
2 stops12h 25mSouthwest
lun. 7/149:15 pmPDX - SJU
1 stop17h 10mSouthwest
Deal found 6/10$495
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/2512:07 pmMBJ - PDX
2 stops25h 10mMultiple Airlines
mié. 7/96:15 amPDX - MBJ
2 stops26h 50mMultiple Airlines
Deal found 6/10$539

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 junio 12, 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

mar. 7/15

4:43 pm-2:15 pm

2 stops24h 32m

Portland

lun. 7/21

3:10 pm-2:45 pm

3 stops20h 35m

$367

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 7/24

12:55 pm-10:15 pm

1 stop12h 20m

Portland

lun. 7/28

11:40 pm-4:04 pm

1 stop13h 24m

$380

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mar. 7/15

4:43 pm-2:15 pm

2 stops24h 32m

Portland

lun. 7/21

9:22 am-3:30 pm

2 stops27h 08m

$383

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

sáb. 9/20

7:30 am-8:25 pm

2 stops15h 55m

Portland

vie. 10/3

10:55 pm-1:10 pm

1 stop11h 15m

$399

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 7/10

12:59 am-12:51 pm

2 stops14h 52m

Portland

lun. 7/14

6:35 am-12:46 am

2 stops15h 11m

$433

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

sáb. 7/19

3:23 pm-9:51 am

1 stop21h 28m

Portland

sáb. 8/16

11:07 pm-10:49 pm

1 stop20h 42m

$440

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

sáb. 7/5

8:53 am-11:17 am

2 stops28h 24m

Portland

sáb. 7/12

3:10 pm-11:00 am

2 stops17h 50m

$461

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

dom. 9/14

3:20 am-12:16 am

2 stops23h 56m

Portland

vie. 9/19

11:36 am-10:51 am

2 stops20h 15m

$483

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

vie. 9/19

1:05 am-1:03 pm

2 stops14h 58m

Portland

vie. 10/3

5:15 pm-12:00 pm

2 stops15h 45m

$489

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

mié. 7/30

12:10 pm-9:18 am

2 stops23h 08m

Portland

sáb. 8/9

3:10 pm-12:45 pm

2 stops19h 35m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 60 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 $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 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 junio 12, 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 junio 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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 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 $185 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $200 and Southwest from $234 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, Kingston Norman Manley - 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 $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?

Book flights to Caribbean 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 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$232Average$392FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$348Average$623FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$585FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$406Average$597FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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