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Caribbean

$318+ Cheap flights from Hawaii to Caribbean

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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Hawaii to Caribbean

Keep the following information in mind while searching for Hawaii to Caribbean flight deals. Data was last updated September 15, 2025.

Round-trip from

$690
(Mytrip)

One-way from

$318
(Trip.com)

Popular in

December

Cheapest in

November

Average price

$810
From Hawaii to Caribbean
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One-way flight from Hawaii to Caribbean
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Highest demand for flights based on searches. 4% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Hawaii to Caribbean

Cheapest flights from Hawaii to Caribbean
Explore the most affordable flight options available from Hawaii to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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.
Mon 11/2411:50 pmHNL - MBJ
3 stops33h 04mWestJet
Sat 11/292:50 pmMBJ - HNL
2 stops29h 05mWestJet
Deal found 9/15$690
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 11/67:00 amHNL - SJU
2 stops16h 20mAmerican Airlines
Wed 11/128:20 amSJU - HNL
2 stops17h 48mAmerican Airlines
Deal found 9/14$785
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Mon 11/242:00 pmHNL - MBJ
2 stops18h 54mMultiple Airlines
Sat 11/292:50 pmMBJ - HNL
2 stops29h 05mMultiple Airlines
Deal found 9/15$792
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 11/810:50 pmHNL - SJU
1 stop13h 35mUnited Airlines
Mon 11/178:10 amSJU - HNL
2 stops18h 53mUnited Airlines
Deal found 9/15$810
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 11/58:45 pmHNL - SJU
1 stop15h 40mUnited Airlines
Tue 11/112:05 amSJU - HNL
2 stops24h 58mUnited Airlines
Deal found 9/15$822
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/299:55 pmHNL - SJU
1 stop14h 30mUnited Airlines
Fri 1/304:52 pmSJU - HNL
2 stops26h 11mUnited Airlines
Deal found 9/15$827
This Air Canada deal was found by Cheapflights users on 9/14. 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.
Wed 10/2210:05 pmHNL - PUJ
2 stops35h 15mAir Canada
Wed 10/292:15 pmPUJ - HNL
2 stops27h 28mAir Canada
Deal found 9/14$842
This Delta deal was found by Cheapflights users on 9/15. 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 10/223:30 pmHNL - PUJ
1 stop14h 58mDelta
Wed 10/292:49 pmPUJ - HNL
2 stops26h 28mDelta
Deal found 9/15$845
This Air Canada deal was found by Cheapflights users on 9/13. 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 10mAir Canada
Sun 11/92:15 amPOS - HNL
2 stops45h 05mAir Canada
Deal found 9/13$849
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 11/610:50 pmHNL - SJU
2 stops16h 36mUnited Airlines
Tue 11/112:05 amSJU - HNL
2 stops24h 58mUnited Airlines
Deal found 9/15$872
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 12/3010:50 pmHNL - SJU
2 stops16h 10mUnited Airlines
Thu 1/292:05 amSJU - HNL
2 stops25h 03mUnited Airlines
Deal found 9/15$877
This Copa Airlines deal was found by Cheapflights users on 9/13. 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 9/13$883

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii 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 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Hawaii to Caribbean that are best for you.

Fly from

Hawaii

Fly to

Caribbean

Route

Depart

Return

Price

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Mon 11/24

11:50 pm-1:54 pm

3 stops33h 04m

Montego Bay Sangster Intl

Sat 11/29

2:50 pm-2:55 pm

2 stops29h 05m

$690

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sun 2/1

12:45 pm-9:26 pm

2 stops26h 41m

San Juan Luis Munoz Marin Intl

Wed 2/18

2:05 am-9:21 pm

2 stops25h 16m

$774

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sun 2/1

5:00 pm-1:00 pm

1 stop14h 00m

San Juan Luis Munoz Marin Intl

Thu 2/19

6:15 am-9:50 pm

2 stops21h 35m

$785

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Wed 11/5

2:36 pm-1:43 pm

2 stops17h 07m

San Juan Luis Munoz Marin Intl

Wed 11/12

6:00 am-10:02 pm

2 stops22h 02m

$785

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Thu 11/6

7:00 am-5:20 am

2 stops16h 20m

San Juan Luis Munoz Marin Intl

Wed 11/12

8:20 am-8:08 pm

2 stops17h 48m

$785

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Mon 11/24

2:00 pm-1:54 pm

2 stops18h 54m

Montego Bay Sangster Intl

Sat 11/29

2:50 pm-2:55 pm

2 stops29h 05m

$792

HonoluluPunta Cana

HNL - PUJ

HNLPUJ

Honolulu

Thu 3/5

5:48 pm-3:53 pm

1 stop16h 05m

Punta Cana

Mon 3/9

4:18 pm-4:35 pm

2 stops30h 17m

$804

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sat 11/8

8:30 pm-4:36 pm

1 stop14h 06m

San Juan Luis Munoz Marin Intl

Sun 11/16

2:05 am-5:05 pm

2 stops21h 00m

$810

HonoluluKingston

HNL - KIN

HNLKIN

Honolulu

Sun 3/1

10:55 pm-1:45 pm

2 stops33h 50m

Kingston Norman Manley

Thu 3/5

2:55 pm-9:40 pm

2 stops35h 45m

$821

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Wed 11/5

6:05 pm-3:40 pm

1 stop15h 35m

San Juan Luis Munoz Marin Intl

Wed 11/12

2:20 pm-12:53 pm

2 stops28h 33m

$822

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 39 results
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Best time to book a flight from Hawaii to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Hawaii to Caribbean (average of $254). Flying from Hawaii to Caribbean 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 CB?

Find hourly flight availability from Hawaii to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

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

Related info for your journey

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

  • How long is the flight from Hawaii to Caribbean?

    WestJet, United Airlines, and Delta can get you from Hawaii to Caribbean in just under 14h. Your travel time can differ by up to 19h 04m. The distance between Hawaii and Caribbean is about 5876 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hawaii 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.

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

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Hawaii to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Hawaii to Caribbean

Discover the top 3 airlines that operate flights from Hawaii 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 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$528Average$940FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$707Average$985FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$744Average$1,190FlexibilityNo cancel feeOn-time71%

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