What is the cheapest airline that flies from Portland to Caribbean Islands?

American Airlines, United Airlines, and Southwest are the most popular carriers operating from Portland to Caribbean Islands

What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Caribbean Islands from Portland according to our data. American Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 6 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?

Prices for flights from Portland Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Portland Airport to Caribbean Islands?

The number of operators available for flights from Portland Airport to Caribbean Islands is 7 as of March 2026.

How old do you have to be to fly from Portland Airport to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$140 Cheap Flights from Portland to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Portland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:40 pm - 1:30 pm

PDX

MBJ

12h 50m

2 stops

4:33 pm - 9:39 am

MBJ

PDX

19h 06m

2 stops

$397United Airlines

mar., mai 26 - dim., mai 31

11:40 pm - 4:15 pm

PDX

STT

13h 35m

2 stops

2:05 pm - 10:20 am

STT

PDX

23h 15m

2 stops

$400American Airlines

mar., mai 5 - mar., mai 12

11:15 pm - 1:08 pm

PDX

STT

10h 53m

1 stop

1:22 pm - 9:59 pm

STT

PDX

11h 37m

1 stop

$425United Airlines

lun., avr. 6 - mar., avr. 21

3:30 pm - 11:26 am

PDX

MBJ

17h 56m

2 stops

4:59 pm - 11:46 am

MBJ

PDX

20h 47m

2 stops

$427Delta

ven., mai 29 - mer., juin 3

7:35 pm - 11:00 am

PDX

SJU

12h 25m

2 stops

5:30 am - 3:00 pm

SJU

PDX

12h 30m

1 stop

$446Southwest

lun., août 17 - lun., août 24

6:05 pm - 12:52 pm

PDX

SJU

15h 47m

2 stops

2:03 pm - 9:42 pm

SJU

PDX

10h 39m

1 stop

$476Delta

mar., avr. 14 - ven., avr. 24

7:35 pm - 11:00 am

PDX

SJU

12h 25m

2 stops

5:00 am - 3:00 pm

SJU

PDX

13h 00m

2 stops

$478Southwest

lun., août 10 - lun., sept. 7

11:47 pm - 2:20 pm

PDX

SJU

11h 33m

1 stop

5:45 am - 11:53 pm

SJU

PDX

21h 08m

1 stop

$493American Airlines

mar., avr. 21 - lun., mai 4

2:30 pm - 1:53 pm

PDX

CUR

20h 23m

2 stops

2:51 pm - 1:04 pm

CUR

PDX

25h 13m

2 stops

$699JetBlue

sam., juin 6 - dim., juin 14

2:30 pm - 5:18 pm

PDX

PUJ

23h 48m

1 stop

11:38 am - 1:10 pm

PUJ

PDX

28h 32m

1 stop

$706JetBlue

ven., mai 29 - lun., juin 1

JetBlue flights from Portland to Caribbean Islands

Our best JetBlue deals on Portland to Caribbean Islands flight tickets

JetBlue

Jun 8

PDX2:30 pmPortland

23h 07m

1 stop

SJU4:37 pmSan Juan Luis Munoz Marin Intl

Jun 13

SJU8:26 pmSan Juan Luis Munoz Marin Intl

19h 38m

1 stop

PDX1:04 pmPortland

$612

JetBlue

Jun 5

PDX2:30 pmPortland

24h 21m

2 stops

SJU5:51 pmSan Juan Luis Munoz Marin Intl

Jun 15

SJU7:55 pmSan Juan Luis Munoz Marin Intl

20h 09m

2 stops

PDX1:04 pmPortland

$615

JetBlue

Jun 6

PDX2:30 pmPortland

20h 23m

2 stops

CUR1:53 pmWillemstad Hato Int.

Jun 14

CUR2:51 pmWillemstad Hato Int.

25h 13m

2 stops

PDX1:04 pmPortland

$699

Southwest flights from Portland to Caribbean Islands

Our best Southwest deals on Portland to Caribbean Islands flight tickets

Southwest

Sep 20

PDX10:45 pmPortland

12h 00m

2 stops

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Sep 27

SJU5:00 amSan Juan Luis Munoz Marin Intl

12h 05m

2 stops

PDX2:05 pmPortland

$446

Southwest

Aug 10

PDX10:45 pmPortland

11h 05m

1 stop

SJU12:50 pmSan Juan Luis Munoz Marin Intl

Sep 7

SJU5:30 amSan Juan Luis Munoz Marin Intl

12h 30m

1 stop

PDX3:00 pmPortland

$478

Southwest

Jul 26

PDX7:25 pmPortland

12h 20m

2 stops

SJU10:45 amSan Juan Luis Munoz Marin Intl

Jul 31

SJU5:30 amSan Juan Luis Munoz Marin Intl

13h 50m

1 stop

PDX4:20 pmPortland

$506

momondo Fare Finder

Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

mar. 5/26

10:40 pm-1:30 pm

2 stops12h 50m

Montego Bay Sangster Intl

dim. 5/31

4:33 pm-9:39 am

2 stops19h 06m

$397

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

mar. 5/5

11:40 pm-4:15 pm

2 stops13h 35m

Saint Thomas Island Cyril E King

mar. 5/12

2:05 pm-10:20 am

2 stops23h 15m

$400

Quickest round-trip

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

lun. 4/6

11:15 pm-1:08 pm

1 stop10h 53m

Saint Thomas Island Cyril E King

mar. 4/21

1:22 pm-9:59 pm

1 stop11h 37m

$425

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

ven. 5/29

3:30 pm-11:26 am

2 stops17h 56m

Montego Bay Sangster Intl

mer. 6/3

4:59 pm-11:46 am

2 stops20h 47m

$427

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 8/17

7:35 pm-11:00 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

lun. 8/24

5:30 am-3:00 pm

1 stop12h 30m

$446

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 4/14

6:05 pm-12:52 pm

2 stops15h 47m

San Juan Luis Munoz Marin Intl

ven. 4/24

2:03 pm-9:42 pm

1 stop10h 39m

$476

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 8/10

7:35 pm-11:00 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

lun. 9/7

5:00 am-3:00 pm

2 stops13h 00m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 4/21

11:47 pm-2:20 pm

1 stop11h 33m

San Juan Luis Munoz Marin Intl

lun. 5/4

5:45 am-11:53 pm

1 stop21h 08m

$493

PortlandWillemstad

PDX - CUR

PDXCUR

Portland

sam. 6/6

2:30 pm-1:53 pm

2 stops20h 23m

Willemstad Hato Int.

dim. 6/14

2:51 pm-1:04 pm

2 stops25h 13m

$699

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

ven. 5/29

2:30 pm-5:18 pm

1 stop23h 48m

Punta Cana

lun. 6/1

11:38 am-1:10 pm

1 stop28h 32m

$706

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $479. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $498.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $576 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Portland for as low as $507 on momondo.

Can stopping save me money on Portland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Portland to Caribbean Islands.

Cheap Portland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Caribbean Islands

Fastest flight time	8h 45m
Direct flights	None

The fastest flight from Portland to Caribbean Islands takes 8h 45m

There are no direct flights from Portland to Caribbean Islands. There are no popular flight routes from Portland to Caribbean Islands.

Search flight deals

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?
Prices for flights from Portland Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Portland Airport to Caribbean Islands?
The number of operators available for flights from Portland Airport to Caribbean Islands is 7 as of March 2026.
How old do you have to be to fly from Portland Airport to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Portland to Caribbean Islands is Boeing 737-800 Passenger/BBJ2 (winglets), representing 22.11% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.65%, Boeing 737-800 at 9.14%, and Airbus A321neo at 7.15%.

Best airlines flying from Portland to Caribbean Islands

Compare and see reviews for airlines that fly from Portland to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $184	Free Cancellation	Rating 7.9 8,350 reviews	Search Delta flights
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,909 reviews	Search JetBlue flights
United Airlines	PriceFrom $224	Free Cancellation	Rating 7.4 9,500 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $241	Free Cancellation	Rating 6.3 8,551 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $399	Free Cancellation	Rating 7.1 11,514 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 8.0 4,334 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Caribbean Islands?

It is quick and easy to find Portland to Caribbean Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean Islands that suits you.

Can I find flights from Portland to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Portland to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean Islands?

momondo helps you find the best flight between Portland and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Portland to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Portland to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.