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

Frontier, Delta, and American Airlines are the most popular carriers operating from Oregon 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 Oregon according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How long is the flight from Oregon to Caribbean Islands?

The flight from Oregon to Caribbean Islands depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Medford (a popular airport in Oregon) to Los Angeles (the most popular airport in Caribbean Islands), then the flight time is 1h 58m on average. If you fly from Eugene (another popular airport in Oregon) to Los Angeles, then the average flight time is 2h 12m.

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

Prices for flights from Oregon to Caribbean Islands were last updated today.

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

As of November 2025, there are 7 operators available to choose from for flights from Oregon to Caribbean Islands.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Caribbean Islands.

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

The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$180 Cheap Flights from Oregon to Caribbean Islands in 2025/26

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Cheap round-trip flights

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11:40 pm - 4:05 pmPDX-SJU

13h 25m1 stop

1:45 pm - 10:25 pmSJU-PDX

11h 40m1 stop

$376JetBlue

Find Deal

Thu, Apr 30 - Sat, May 16

8:45 am - 12:10 amPDX-SJU

11h 25m2 stops

5:30 am - 2:55 pmSJU-PDX

13h 25m2 stops

$397Southwest

Find Deal

Sat, Feb 7 - Thu, Feb 12

7:37 pm - 4:49 pmPDX-SJU

17h 12m2 stops

3:55 pm - 10:15 pmSJU-PDX

10h 20m1 stop

$419Delta

Find Deal

Thu, Jan 8 - Wed, Jan 14

7:00 am - 9:00 pmPDX-SJU

10h 00m1 stop

2:05 am - 1:45 pmSJU-PDX

15h 40m2 stops

$448United Airlines

Find Deal

Thu, Jan 8 - Mon, Jan 12

12:40 am - 5:17 pmPDX-SJU

12h 37m2 stops

7:30 am - 6:50 pmSJU-PDX

15h 20m2 stops

$457Delta

Find Deal

Tue, Jan 20 - Wed, Jan 28

3:50 pm - 4:36 pmPDX-SJU

20h 46m2 stops

2:05 am - 11:06 pmSJU-PDX

25h 01m2 stops

$458United Airlines

Find Deal

Mon, Jan 19 - Tue, Jan 27

10:45 pm - 1:43 pmPDX-SJU

10h 58m1 stop

2:36 pm - 11:23 pmSJU-PDX

12h 47m2 stops

$459American Airlines

Find Deal

Mon, Dec 1 - Mon, Dec 8

2:13 pm - 3:32 pmPDX-STI

21h 19m2 stops

6:00 am - 7:02 pmSTI-PDX

17h 02m2 stops

$472American Airlines

Find Deal

Sat, Jan 10 - Sat, Jan 17

7:29 am - 2:07 pmPDX-MBJ

27h 38m1 stop

3:31 pm - 8:50 pmMBJ-PDX

32h 19m1 stop

$501Multiple Airlines

Find Deal

Wed, Dec 3 - Mon, Dec 8

7:05 am - 5:12 pmPDX-PUJ

30h 07m1 stop

7:30 pm - 4:44 pmPUJ-PDX

25h 14m2 stops

$504Multiple Airlines

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Fri, Jan 30 - Tue, Feb 3

JetBlue flights from Oregon to Caribbean Islands

Our best JetBlue deals on Oregon to Caribbean Islands flight tickets

JetBlue

Apr 30

PDX11:40 pmPortland

13h 25m

1 stop

SJU4:05 pmSan Juan Luis Munoz Marin Intl

May 16

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$376

Find similar

JetBlue

May 2

PDX11:40 pmPortland

22h 19m

2 stops

SJU12:59 amSan Juan Luis Munoz Marin Intl

May 16

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$410

Find similar

JetBlue

Apr 29

PDX11:40 pmPortland

13h 25m

1 stop

SJU4:05 pmSan Juan Luis Munoz Marin Intl

May 17

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 40m

1 stop

PDX10:25 pmPortland

$430

Find similar

Southwest flights from Oregon to Caribbean Islands

Our best Southwest deals on Oregon to Caribbean Islands flight tickets

Southwest

Feb 7

PDX8:45 amPortland

11h 25m

2 stops

SJU12:10 amSan Juan Luis Munoz Marin Intl

Feb 12

SJU5:30 amSan Juan Luis Munoz Marin Intl

13h 25m

2 stops

PDX2:55 pmPortland

$397

Find similar

Southwest

Dec 10

PDX8:00 amPortland

12h 35m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Dec 16

SJU11:20 amSan Juan Luis Munoz Marin Intl

14h 05m

2 stops

PDX9:25 pmPortland

$435

Find similar

Southwest

Feb 22

PDX6:50 pmPortland

11h 40m

2 stops

SJU10:30 amSan Juan Luis Munoz Marin Intl

Feb 28

SJU10:55 amSan Juan Luis Munoz Marin Intl

15h 35m

2 stops

PDX10:30 pmPortland

$444

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 4/30

11:40 pm-4:05 pm

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Sat 5/16

1:45 pm-10:25 pm

1 stop11h 40m

$376

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/7

8:45 am-12:10 am

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Thu 2/12

5:30 am-2:55 pm

2 stops13h 25m

$397

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/8

7:37 pm-4:49 pm

2 stops17h 12m

San Juan Luis Munoz Marin Intl

Wed 1/14

3:55 pm-10:15 pm

1 stop10h 20m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/8

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Mon 1/12

2:05 am-1:45 pm

2 stops15h 40m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/20

12:40 am-5:17 pm

2 stops12h 37m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:30 am-6:50 pm

2 stops15h 20m

$457

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

3:50 pm-4:36 pm

2 stops20h 46m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-11:06 pm

2 stops25h 01m

$458

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 12/1

10:45 pm-1:43 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Mon 12/8

2:36 pm-11:23 pm

2 stops12h 47m

$459

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Sat 1/10

2:13 pm-3:32 pm

2 stops21h 19m

Santiago de los Caballeros

Sat 1/17

6:00 am-7:02 pm

2 stops17h 02m

$472

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 12/3

7:29 am-2:07 pm

1 stop27h 38m

Montego Bay Sangster Intl

Mon 12/8

3:31 pm-8:50 pm

1 stop32h 19m

$501

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 1/30

7:05 am-5:12 pm

1 stop30h 07m

Punta Cana

Tue 2/3

7:30 pm-4:44 pm

2 stops25h 14m

$504

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How to get the cheapest flight ticket from Oregon 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

Other information

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 Oregon, with most prices found around $449. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Oregon averaging around $485.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Oregon to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $454. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $655. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Oregon to Caribbean Islands in the afternoon for as low as $428. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $602. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Caribbean Islands from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $577 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Oregon for as low as $479 on momondo.

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

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

Cheap Oregon to Caribbean Islands flight deals and tips

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

Direct flights	None

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

Search flight deals

When did momondo last update prices for flights from Oregon to Caribbean Islands?
Prices for flights from Oregon to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Oregon to Caribbean Islands?
As of November 2025, there are 7 operators available to choose from for flights from Oregon to Caribbean Islands.
How old do you have to be to fly from Oregon to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Oregon to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Oregon to Caribbean Islands is Boeing 737-800 Passenger/BBJ2 (winglets), representing 15.09% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 10.80%, Boeing 737-900 Passenger/BBJ3 (winglets) at 10.03%, and Boeing 737 MAX 9 at 9.26%.

Best airlines flying from Oregon to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $185	Free Cancellation	Rating 7.2 2,908 reviews	Search JetBlue flights
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Spirit Airlines	PriceFrom $248	Free Cancellation	Rating 6.3 8,132 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $343	Free Cancellation	Rating 7.2 11,046 reviews	Search American Airlines flights
United Airlines	PriceFrom $394	Free Cancellation	Rating 7.4 9,014 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $431	Free Cancellation	Rating 8.0 11,255 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $444	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Oregon.

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

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oregon to Caribbean Islands.

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

Price alerts on flights to Caribbean Islands from Oregon are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Flights to Los Angelesfrom $51

Flights to Parisfrom $340

Flights to Copenhagenfrom $360

Flights to Istanbulfrom $374

Flights to Manilafrom $521

Flights to Romefrom $320

Flights to Miamifrom $48

Flights to Chicagofrom $58

Cheap flights from Oregon to Caribbean Islands from $180

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Caribbean Islands departing on 12/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Find the cheapest flights from Oregon to Caribbean Islands

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JetBlue flights from Oregon to Caribbean Islands

Our best JetBlue deals on Oregon to Caribbean Islands flight tickets

Southwest flights from Oregon to Caribbean Islands

Our best Southwest deals on Oregon to Caribbean Islands flight tickets

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How to get the cheapest flight ticket from Oregon 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

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 Oregon, with most prices found around $449. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Oregon averaging around $485.

What is the cheapest day to depart on your flight to Caribbean Islands?

What is the cheapest time of day to depart on your flight to Caribbean Islands?

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

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

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

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

Frontier, Delta, and American Airlines are the most popular carriers operating from Oregon to Caribbean Islands

What airlines fly to Caribbean Islands?

How long is the flight from Oregon to Caribbean Islands?

Cheap Oregon to Caribbean Islands flight deals and tips

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

Direct flights

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

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

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

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

What is the most popular plane model from Oregon to Caribbean Islands?

Best airlines flying from Oregon to Caribbean Islands

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

Why use momondo?

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

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

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

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

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo