Cheap flights from Portland (PWM) to Caribbean from $109

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 5/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
PWM — SJU
May 9 — May 161

How far in advance should I book a flight from Portland, Maine to Caribbean?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 48 days in advance, which can save you up to 81% on flights from Portland, Maine to Caribbean compared to booking the week you need them. Waiting 48 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $515. For sooner than that we have options available in the next 3 days from $690.

What is the cheapest month to fly from Portland, Maine to Caribbean?

Our data shows that October tends to be the cheapest month to fly to Caribbean from Portland, Maine. Users have commonly found prices around $524 for the month, but tickets can be as low as $292. Due to multiple factors, prepare for potentially higher prices in November.

When is the cheapest time to fly from Portland, Maine to Caribbean (PWM - CB)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Caribbean as you normally would.

Cheap Delta flights from Portland to Caribbean

Explore cheap flight options specifically provided by Delta for the route between Portland and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Fri 6/1412:40 pmSJU - PWM
1 stop11h 44mDelta
Deal found 5/3$284
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Sat 6/155:42 pmSJU - PWM
1 stop6h 42mDelta
Deal found 5/4$303
Tue 6/252:08 pmPWM - SJU
1 stop10h 08mDelta
Fri 7/57:00 amSJU - PWM
1 stop8h 06mDelta
Deal found 5/2$322
Mon 6/172:08 pmPWM - SJU
1 stop10h 08mDelta
Tue 6/2512:40 pmSJU - PWM
1 stop11h 44mDelta
Deal found 5/2$344
Tue 6/116:15 amPWM - NAS
1 stop10h 47mDelta
Thu 6/136:27 pmNAS - PWM
1 stop20h 39mDelta
Deal found 5/2$353
Tue 6/115:26 pmPWM - NAS
2 stops23h 36mDelta
Thu 6/136:27 pmNAS - PWM
1 stop20h 39mDelta
Deal found 5/2$358
Tue 6/252:08 pmPWM - SJU
1 stop10h 08mDelta
Thu 7/412:52 pmSJU - PWM
1 stop9h 06mDelta
Deal found 5/2$363
Thu 9/195:30 amPWM - AUA
1 stop7h 30mDelta
Mon 9/232:15 pmAUA - PWM
1 stop9h 23mDelta
Deal found 5/3$380
Mon 9/236:05 amPWM - PUJ
1 stop8h 58mDelta
Wed 9/251:55 pmPUJ - PWM
1 stop9h 43mDelta
Deal found 5/2$397

Cheap Frontier flights from Portland to Caribbean

Explore cheap flight options specifically provided by Frontier for the route between Portland and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Sat 5/186:48 amSJU - PWM
1 stop28h 02mFrontier
Deal found 5/2$218
Thu 6/271:57 pmPWM - SJU
1 stop9h 29mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$290
Sun 6/91:57 pmPWM - SJU
1 stop12h 08mFrontier
Sat 6/1510:15 pmSJU - PWM
1 stop10h 51mFrontier
Deal found 5/3$294
Tue 6/2511:40 amPWM - SJU
1 stop20h 42mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$310
Sun 6/2310:06 amPWM - SJU
1 stop8h 43mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$314
Tue 6/253:23 pmPWM - PUJ
2 stops19h 08mFrontier
Mon 7/112:11 pmPUJ - PWM
2 stops33h 15mFrontier
Deal found 5/3$365
Tue 6/259:55 pmPWM - PUJ
1 stop13h 04mFrontier
Mon 7/112:11 pmPUJ - PWM
2 stops33h 15mFrontier
Deal found 5/3$368
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Fri 5/173:15 amSJU - PWM
1 stop29h 54mFrontier
Deal found 5/2$390
Thu 6/610:08 amPWM - SXM
2 stops31h 07mFrontier
Mon 6/106:25 pmSXM - PWM
2 stops14h 41mFrontier
Deal found 5/3$423

Cheap Portland to Caribbean flights in May & June 2024

Find cheap flight options from Portland to Caribbean specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Prices were last updated on May 4, 2024.
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Sat 5/186:48 amSJU - PWM
1 stop28h 02mFrontier
Deal found 5/2$218
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Sat 6/155:42 pmSJU - PWM
1 stop6h 42mDelta
Deal found 5/3$284
Thu 6/271:57 pmPWM - SJU
1 stop9h 29mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$290
Sun 6/91:57 pmPWM - SJU
1 stop12h 08mFrontier
Sat 6/1510:15 pmSJU - PWM
1 stop10h 51mFrontier
Deal found 5/3$294
Tue 6/257:54 pmPWM - SJU
1 stop7h 03mJetBlue
Thu 7/412:30 pmSJU - PWM
1 stop6h 29mJetBlue
Deal found 5/3$302
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Sat 6/155:42 pmSJU - PWM
1 stop6h 42mDelta
Deal found 5/4$303
Mon 6/247:54 pmPWM - SJU
1 stop6h 03mJetBlue
Thu 7/411:19 amSJU - PWM
1 stop7h 40mJetBlue
Deal found 5/2$304
Tue 6/2511:40 amPWM - SJU
1 stop20h 42mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$310
Sun 6/2310:06 amPWM - SJU
1 stop8h 43mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$314

Portland to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Portland and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Sat 5/186:48 amSJU - PWM
1 stop28h 02mFrontier
Deal found 5/2$218
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Sat 6/155:42 pmSJU - PWM
1 stop6h 42mDelta
Deal found 5/3$284
Thu 6/271:57 pmPWM - SJU
1 stop9h 29mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$290
Sun 6/91:57 pmPWM - SJU
1 stop12h 08mFrontier
Sat 6/1510:15 pmSJU - PWM
1 stop10h 51mFrontier
Deal found 5/3$294
Tue 6/257:54 pmPWM - SJU
1 stop7h 03mJetBlue
Thu 7/412:30 pmSJU - PWM
1 stop6h 29mJetBlue
Deal found 5/3$302
Tue 8/206:01 amPWM - AUA
1 stop7h 01mAmerican Airlines
Tue 8/274:57 pmAUA - PWM
2 stops18h 39mAmerican Airlines
Deal found 5/2$303
Fri 6/72:08 pmPWM - SJU
1 stop10h 08mDelta
Sat 6/155:42 pmSJU - PWM
1 stop6h 42mDelta
Deal found 5/4$303
Mon 6/247:54 pmPWM - SJU
1 stop6h 03mJetBlue
Thu 7/411:19 amSJU - PWM
1 stop7h 40mJetBlue
Deal found 5/2$304
Tue 6/2511:40 amPWM - SJU
1 stop20h 42mFrontier
Wed 7/310:15 pmSJU - PWM
1 stop10h 56mFrontier
Deal found 5/2$310

Portland to Caribbean flights leaving soon

Find last-minute flight options from Portland to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Sat 5/186:48 amSJU - PWM
1 stop28h 02mFrontier
Deal found 5/2$218
Sun 5/129:40 amPWM - SJU
1 stop16h 16mFrontier
Fri 5/173:15 amSJU - PWM
1 stop29h 54mFrontier
Deal found 5/2$390
Sat 5/117:45 amPWM - PLS
1 stop26h 45mAmerican Airlines
Tue 5/211:30 pmPLS - PWM
2 stops10h 17mAmerican Airlines
Deal found 5/3$546
Mon 5/136:05 amPWM - PLS
1 stop6h 30mDelta
Sat 5/182:00 pmPLS - PWM
1 stop7h 59mDelta
Deal found 5/3$567
Sat 5/117:45 amPWM - PLS
1 stop26h 45mAmerican Airlines
Tue 5/213:20 pmPLS - PWM
1 stop21h 06mAmerican Airlines
Deal found 5/3$587
Sat 5/111:05 pmPWM - PLS
2 stops21h 25mAmerican Airlines
Tue 5/211:30 pmPLS - PWM
2 stops10h 17mAmerican Airlines
Deal found 5/3$610
Sun 5/126:05 amPWM - SJU
2 stops14h 33mUnited Airlines
Sat 5/181:24 pmSJU - PWM
1 stop8h 28mUnited Airlines
Deal found 5/2$621
Sat 5/1112:08 pmPWM - STT
2 stops21h 26mMultiple Airlines
Fri 5/1710:26 amSTT - PWM
3 stops25h 01mMultiple Airlines
Deal found 5/3$634
Sat 5/1112:08 pmPWM - STT
3 stops24h 53mMultiple Airlines
Fri 5/1710:26 amSTT - PWM
3 stops25h 01mMultiple Airlines
Deal found 5/3$640

One-way flights to Caribbean from Portland

Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Fri 5/1012:56 pmPWM - SJU
1 stop13h 23mFrontier
Deal found 5/3$109
Thu 5/91:00 pmPWM - SJU
1 stop13h 15mFrontier
Deal found 5/3$169
Fri 7/57:35 amPWM - AUA
2 stops30h 05mAmerican Airlines
Deal found 5/3$173
Sat 7/67:45 amPWM - AUA
2 stops32h 00mAmerican Airlines
Deal found 5/3$243
Fri 7/55:05 amPWM - AUA
1 stop7h 55mDelta
Deal found 5/3$247
Sun 7/78:44 pmPWM - AUA
1 stop14h 46mAmerican Airlines
Deal found 5/3$259
Sat 8/35:13 pmPWM - AUA
2 stops20h 27mAmerican Airlines
Deal found 5/3$264
Sun 6/307:22 pmPWM - AUA
2 stops18h 28mUnited Airlines
Deal found 5/3$287
Fri 5/105:30 pmPWM - SJU
2 stops19h 10mAmerican Airlines
Deal found 5/3$292

Find flights from Portland to Caribbean within your budget

Customize your flight search to find flights from Portland to Caribbean 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 2,864,334 searches. Data last updated May 4, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$284 - $488

Route

Depart

Return

Price

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Fri 6/7

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Fri 6/14

1 stop11h 44m

$284

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Thu 6/27

1 stop9h 29m

San Juan Luis Munoz Marin Intl

Wed 7/3

1 stop10h 56m

$290

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Sun 6/9

1 stop12h 08m

San Juan Luis Munoz Marin Intl

Sat 6/15

1 stop10h 51m

$294

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Tue 6/25

1 stop7h 03m

San Juan Luis Munoz Marin Intl

Thu 7/4

1 stop6h 29m

$302

PortlandOranjestad Reina Beatrix

PWM - AUA

PWMAUA

Portland

Tue 8/20

1 stop7h 01m

Oranjestad Reina Beatrix

Tue 8/27

2 stops18h 39m

$303

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Fri 6/7

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Sat 6/15

1 stop6h 42m

$303

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Mon 6/24

1 stop6h 03m

San Juan Luis Munoz Marin Intl

Thu 7/4

1 stop7h 40m

$304

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Sun 6/2

2 stops22h 23m

San Juan Luis Munoz Marin Intl

Sun 6/9

2 stops28h 29m

$478

PortlandSan Juan Luis Munoz Marin Intl

PWM - SJU

PWMSJU

Portland

Tue 6/11

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 6/17

1 stop7h 19m

$488

Flights are sorted by cheapest first

Deals found on 5/3

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated May 4, 2024.
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

8.1
Very good
10,838 reviews
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.6
Good
4,545 reviews
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.4
Good
11,125 reviews
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.3
Good
14,728 reviews
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

6.3
Okay
4,098 reviews
8.1
Very good
10,838 reviews

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean. 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 from for flights from Portland to Caribbean?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Caribbean. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

  • Can I find flights from Portland, Maine to Caribbean for under $300 on Cheapflights?

    Yes, there are multiple flights from Portland, Maine to Caribbean for under $300. The cheapest flight booked recently is on Delta for just $284, but on average you can expect to pay $326.

  • Are there last-minute flights available from Portland, Maine to Caribbean for under $300?

    There are currently 20+ open flights from Portland, Maine to Caribbean within the next 7 days for less than $300.

  • What are the cheapest airlines to fly from Portland, Maine to Caribbean one-way?

    One-way options have recently been found by users for as low as $109 on Frontier. Other airlines that offer cheap prices include American Airlines from $173 and Delta from $247 one-way.

  • What are the most popular routes from Portland, Maine to Caribbean?

  • What are the most popular airlines that fly from Portland, Maine to Caribbean?

  • What does PWM to SJU mean?

    Portland Airport is PWM and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Nassau Intl Airport (NAS) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Portland to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Portland to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Portland to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Portland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Portland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Caribbean.

  • Can I find deals for business class flights from Portland to Caribbean?

    Yes. Cheapflights offers flight deals from Portland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Portland to Caribbean that allow pets onboard?

    Many airlines flying from Portland to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Portland to Caribbean?

    Yes, you can often find last-minute deals on Portland to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Portland, Maine to Caribbean flight deals updated?

    The Portland, Maine to Caribbean flight deals you see on this page were last updated on 5/4.

See more FAQs

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Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Portland to Caribbean

Discover the top 5 airlines that operate flights from Portland to Caribbean. 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 2,864,334 searches. Data last updated May 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$232Average$289FlexibilityNo cancel feeOn-time62%
Search Frontier flights
DeltaCheapest$271Average$839FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$311Average$653FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$312Average$582FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest$349Average$701FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Search flights from Portland to Caribbean by cabin class

Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Portland to Caribbean?

Cheapflights helps you search for flights from Portland to Caribbean via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Portland to Caribbean?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Portland to Caribbean for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Portland to Caribbean with no change fees?

Need flexible booking options for your flight to Caribbean from Portland? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Portland to Caribbean become cheaper?

Of course! You can now track prices for flights from Portland to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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