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Caribbean Islands

$370+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
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Cheap 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 January 31, 2026.

This American Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 4/97:00 am
HNL
-
AUA
2 stops24h 29m
American Airlines
Tue 4/144:16 pm
AUA
-
HNL
2 stops27h 21m
American Airlines
Deal found 1/29$691
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:00 am
HNL
-
SJU
2 stops23h 04m
United Airlines
Thu 5/71:00 am
SJU
-
HNL
2 stops21h 17m
United Airlines
Deal found 1/29$702
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/31:00 pm
HNL
-
AUA
2 stops17h 40m
United Airlines
Thu 5/74:30 pm
AUA
-
HNL
2 stops25h 24m
United Airlines
Deal found 1/30$741
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
HNL
-
SJU
2 stops23h 04m
United Airlines
Mon 5/41:00 am
SJU
-
HNL
2 stops24h 49m
United Airlines
Deal found 1/29$752
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:45 am
HNL
-
SJU
2 stops21h 57m
United Airlines
Tue 5/51:00 am
SJU
-
HNL
2 stops24h 49m
United Airlines
Deal found 1/29$760
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:10 pm
HNL
-
SJU
2 stops18h 32m
United Airlines
Tue 5/51:00 am
SJU
-
HNL
2 stops24h 49m
United Airlines
Deal found 1/29$779
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
HNL
-
SJU
2 stops23h 04m
United Airlines
Thu 5/73:56 pm
SJU
-
HNL
2 stops25h 58m
United Airlines
Deal found 1/29$782
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/259:00 pm
HNL
-
SJU
2 stops22h 05m
Southwest
Mon 3/95:00 am
SJU
-
HNL
2 stops22h 10m
Southwest
Deal found 1/29$786
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:06 pm
HNL
-
SJU
1 stop19h 52m
Multiple Airlines
Tue 3/106:49 pm
SJU
-
HNL
2 stops24h 29m
Multiple Airlines
Deal found 1/30$787
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:45 am
HNL
-
SJU
2 stops21h 57m
United Airlines
Thu 5/72:55 pm
SJU
-
HNL
2 stops26h 59m
United Airlines
Deal found 1/29$790
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:40 pm
HNL
-
SJU
1 stop13h 58m
United Airlines
Fri 5/87:00 am
SJU
-
HNL
2 stops18h 49m
United Airlines
Deal found 1/30$798
This Delta deal was found by Cheapflights users on 1/29. 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 4/2712:31 pm
HNL
-
SJU
2 stops22h 00m
Delta
Thu 5/76:15 am
SJU
-
HNL
2 stops20h 32m
Delta
Deal found 1/29$806

Find 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 January 31, 2026.

Round-trip from

$691
(American Airlines)

One-way from

$370
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$945
From Hawaii to Caribbean Islands
Search Deals
One-way flight from Hawaii to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 31, 2026.
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

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Thu 4/9

7:00 am-1:29 pm

2 stops24h 29m

Oranjestad Reina Beatrix

Tue 4/14

4:16 pm-1:37 pm

2 stops27h 21m

$691

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 5/5

1:00 pm-5:38 pm

2 stops22h 38m

San Juan Luis Munoz Marin Intl

Thu 5/7

1:00 am-4:17 pm

2 stops21h 17m

$702

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Sun 5/3

1:00 pm-12:40 pm

2 stops17h 40m

Oranjestad Reina Beatrix

Thu 5/7

4:30 pm-11:54 am

2 stops25h 24m

$741

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 4/28

7:00 am-12:04 pm

2 stops23h 04m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-7:49 pm

2 stops24h 49m

$752

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 4/24

11:45 am-3:42 pm

2 stops21h 57m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-7:49 pm

2 stops24h 49m

$760

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 4/27

9:40 pm-11:50 pm

2 stops20h 10m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-7:49 pm

2 stops24h 49m

$779

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sat 4/25

3:10 pm-3:42 pm

2 stops18h 32m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-7:49 pm

2 stops24h 49m

$779

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 4/27

7:40 pm-11:50 pm

2 stops22h 10m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-7:49 pm

2 stops24h 49m

$779

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sun 4/26

9:40 pm-11:50 pm

2 stops20h 10m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-7:49 pm

2 stops24h 49m

$779

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 5/1

9:25 pm-9:25 pm

2 stops18h 00m

San Juan Luis Munoz Marin Intl

Fri 5/8

10:00 am-9:05 pm

2 stops17h 05m

$786

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 42 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, May is the cheapest month in which you can book a flight from Hawaii to Caribbean Islands (average of $448). Flying from Hawaii to Caribbean Islands in July is currently the most expensive (average of $1,066). 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.

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.

  • How long is the flight from Hawaii to Caribbean Islands?

    Airlines like American Airlines, United Airlines, and Air Canada fly from Hawaii to Caribbean Islands in about 22h 38m. The time it takes to get you to your destination can typically vary by up to 33h 47m. The distance between Hawaii and Caribbean Islands is about 5876 mi. This flight may include one or multiple stops.

  • 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, May is the cheapest month in which you can book a flight from Hawaii to Caribbean Islands (average of $448). Flying from Hawaii to Caribbean Islands in July is currently the most expensive (average of $1,066). 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 Islands

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 Islands

Discover the top 3 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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$412Average$1,010FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$516Average$1,232FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$755Average$1,010FlexibilityNo cancel feeOn-time71%

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