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Caribbean Islands

$356+ Cheap flights from Hawaii to Caribbean Islands

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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Hawaii to Caribbean Islands

Keep the following information in mind while searching for Hawaii to Caribbean Islands flight deals. Data was last updated July 31, 2025.

Round-trip from

$729
(United Airlines)

One-way from

$356
(United Airlines)

Popular in

July

Cheapest in

August

Average price

$1,210
From Hawaii to Caribbean Islands
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One-way flight from Hawaii to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Hawaii to Caribbean Islands

Cheapest flights from Hawaii to Caribbean Islands
Explore the most affordable flight options available from Hawaii to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/198:00 amHNL - SJU
2 stops24h 44mUnited Airlines
Thu 9/254:55 pmSJU - HNL
2 stops24h 23mUnited Airlines
Deal found 7/31$729
This Air Canada deal was found by Cheapflights users on 7/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:00 pmHNL - POS
2 stops29h 15mAir Canada
Sun 11/92:15 amPOS - HNL
2 stops40h 28mAir Canada
Deal found 7/29$764
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/52:15 pmHNL - SJU
2 stops20h 55mDelta
Wed 11/127:30 amSJU - HNL
2 stops18h 50mDelta
Deal found 7/29$785
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/55:30 pmHNL - SJU
1 stop14h 45mAmerican Airlines
Fri 9/196:10 amSJU - HNL
2 stops17h 44mAmerican Airlines
Deal found 7/30$805
This Copa Airlines deal was found by Cheapflights users on 7/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:00 amHNL - AUA
2 stops46h 10mCopa Airlines
Thu 11/133:47 pmAUA - HNL
2 stops35h 16mCopa Airlines
Deal found 7/30$834
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sat 11/110:50 pmHNL - MBJ
3 stops32h 15mMultiple Airlines
Fri 11/145:45 pmMBJ - HNL
2 stops47h 58mMultiple Airlines
Deal found 7/30$842
This Copa Airlines deal was found by Cheapflights users on 7/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:25 pmHNL - POS
2 stops29h 23mCopa Airlines
Mon 11/102:26 pmPOS - HNL
2 stops36h 37mCopa Airlines
Deal found 7/29$883
This Delta deal was found by Cheapflights users on 7/31. 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.
Mon 9/83:25 pmHNL - STI
1 stop15h 18mDelta
Sun 9/218:40 pmSTI - HNL
1 stop23h 08mDelta
Deal found 7/31$895
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/13:05 pmHNL - SDQ
1 stop16h 17mDelta
Sun 9/147:40 pmSDQ - HNL
1 stop24h 08mDelta
Deal found 7/29$895
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:00 pmHNL - SDQ
2 stops16h 23mAmerican Airlines
Fri 12/55:50 pmSDQ - HNL
2 stops25h 21mAmerican Airlines
Deal found 7/29$979
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:05 pmHNL - MBJ
1 stop14h 41mUnited Airlines
Fri 11/141:25 pmMBJ - HNL
2 stops28h 28mUnited Airlines
Deal found 7/30$996
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/88:00 amHNL - STI
3 stops25h 12mUnited Airlines
Fri 9/192:07 pmSTI - HNL
2 stops27h 11mUnited Airlines
Deal found 7/31$1,009

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii to Caribbean Islands 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 July 31, 2025.
Use the filters below to find and compare flights from Hawaii to Caribbean Islands that are best for you.

Fly from

Hawaii

Fly to

Caribbean Islands

Route

Depart

Return

Price

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 9/19

8:00 am-2:44 pm

2 stops24h 44m

San Juan Luis Munoz Marin Intl

Thu 9/25

4:55 pm-11:18 am

2 stops24h 23m

$729

HonoluluPort of Spain

HNL - POS

HNLPOS

Honolulu

Thu 11/6

2:00 pm-1:15 am

2 stops29h 15m

Port of Spain Piarco Intl

Sun 11/9

2:15 am-12:43 pm

2 stops40h 28m

$764

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Wed 11/5

2:15 pm-5:10 pm

2 stops20h 55m

San Juan Luis Munoz Marin Intl

Wed 11/12

7:30 am-8:20 pm

2 stops18h 50m

$785

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 9/5

5:30 pm-2:15 pm

1 stop14h 45m

San Juan Luis Munoz Marin Intl

Fri 9/19

6:10 am-5:54 pm

2 stops17h 44m

$805

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Tue 11/11

8:00 am-12:10 pm

2 stops46h 10m

Oranjestad Reina Beatrix

Thu 11/13

3:47 pm-9:03 pm

2 stops35h 16m

$834

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Sat 11/1

10:50 pm-12:05 pm

3 stops32h 15m

Montego Bay Sangster Intl

Fri 11/14

5:45 pm-12:43 pm

2 stops47h 58m

$842

HonoluluPort of Spain

HNL - POS

HNLPOS

Honolulu

Thu 11/6

2:25 pm-1:48 am

2 stops29h 23m

Port of Spain Piarco Intl

Mon 11/10

2:26 pm-9:03 pm

2 stops36h 37m

$883

HonoluluSantiago de los Caballeros

HNL - STI

HNLSTI

Honolulu

Mon 9/8

3:25 pm-12:43 pm

1 stop15h 18m

Santiago de los Caballeros

Sun 9/21

8:40 pm-1:48 pm

1 stop23h 08m

$895

HonoluluSanto Domingo

HNL - SDQ

HNLSDQ

Honolulu

Mon 9/1

3:05 pm-1:22 pm

1 stop16h 17m

Santo Domingo Las Americas

Sun 9/14

7:40 pm-1:48 pm

1 stop24h 08m

$895

HonoluluSanto Domingo

HNL - SDQ

HNLSDQ

Honolulu

Mon 12/1

7:00 pm-5:23 pm

2 stops16h 23m

Santo Domingo Las Americas

Fri 12/5

5:50 pm-1:11 pm

2 stops25h 21m

$979

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 28 results
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Best time to book a flight from Hawaii to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Hawaii 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 Hawaii to Caribbean Islands

What is the cheapest month to book a flight from Hawaii to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Hawaii to Caribbean Islands (average of $254). Flying from Hawaii to Caribbean Islands in June is currently the most expensive (average of $339). 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 HI to EPX?

Find hourly flight availability from Hawaii to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Hawaii to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated July 31, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Hawaii to Caribbean Islands to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Copa Airlines
7.5
Good
1,493 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Hawaii to Caribbean Islands one-way?

    $356 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Alaska Airlines, with prices starting from $438 and $462, respectively.

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

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

  • How can I find direct flights from Hawaii to Caribbean Islands?

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

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

    Yes. Cheapflights offers flight deals from Hawaii to Caribbean Islands 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 Hawaii to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Hawaii to Caribbean Islands (average of $254). Flying from Hawaii to Caribbean Islands in June is currently the most expensive (average of $339). 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

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Alternative routes for Hawaii to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Hawaii to Caribbean Islands

Discover the top 4 airlines that operate flights from Hawaii to Caribbean Islands. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$474Average$1,052FlexibilityNo cancel feeOn-time62%
DeltaCheapest$528Average$894FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$707Average$987FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$711Average$1,062FlexibilityNo cancel feeOn-time71%

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