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$371+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 January 28, 2026.

This Air Canada deal was found by Cheapflights users on 1/27. 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 4/301:00 pm
HNL
-
NAS
2 stops46h 30m
Air Canada
Thu 5/76:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$656
This Air Canada deal was found by Cheapflights users on 1/27. 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 4/301:00 pm
HNL
-
NAS
2 stops46h 30m
Air Canada
Wed 5/66:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$692
This United Airlines deal was found by Cheapflights users on 1/25. 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 stops25h 44m
United Airlines
Thu 5/71:00 am
SJU
-
HNL
2 stops24h 49m
United Airlines
Deal found 1/25$702
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Tue 5/59:55 pm
HNL
-
NAS
2 stops32h 45m
Air Canada
Thu 5/76:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$757
This Air Canada deal was found by Cheapflights users on 1/27. 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 4/301:00 pm
HNL
-
NAS
2 stops46h 30m
Air Canada
Tue 5/56:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$762
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Mon 5/49:55 pm
HNL
-
NAS
2 stops37h 35m
Air Canada
Thu 5/76:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$796
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/247:50 am
HNL
-
SJU
2 stops25h 16m
Multiple Airlines
Tue 3/37:10 am
SJU
-
HNL
1 stop38h 07m
Multiple Airlines
Deal found 1/27$797
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/2610:55 pm
HNL
-
AUA
2 stops35h 45m
United Airlines
Mon 3/23:00 pm
AUA
-
HNL
2 stops32h 35m
United Airlines
Deal found 1/26$812
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/249:30 pm
HNL
-
SJU
2 stops19h 40m
Southwest
Tue 3/36:10 am
SJU
-
HNL
2 stops20h 50m
Southwest
Deal found 1/27$821
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/56:45 pm
HNL
-
PUJ
2 stops15h 51m
American Airlines
Mon 3/94:43 pm
PUJ
-
HNL
2 stops24h 31m
American Airlines
Deal found 1/27$825
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/96:00 pm
HNL
-
SJU
1 stop15h 28m
American Airlines
Tue 3/246:33 am
SJU
-
HNL
2 stops19h 48m
American Airlines
Deal found 1/27$826
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Sun 5/39:55 pm
HNL
-
NAS
2 stops37h 35m
Air Canada
Thu 5/76:30 pm
NAS
-
HNL
2 stops32h 10m
Air Canada
Deal found 1/27$834

Find flight deals from Hawaii to Caribbean

Keep the following information in mind while searching for Hawaii to Caribbean flight deals. Data was last updated January 28, 2026.

Round-trip from

$656
(Air Canada)

One-way from

$371
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$945
From Hawaii to Caribbean
Search Deals
One-way flight from Hawaii to Caribbean
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 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 28, 2026.
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

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 5/5

7:00 am-2:44 pm

2 stops25h 44m

San Juan Luis Munoz Marin Intl

Thu 5/7

1:00 am-7:49 pm

2 stops24h 49m

$702

HonoluluNassau

HNL - NAS

HNLNAS

Honolulu

Mon 5/4

9:55 pm-5:30 pm

2 stops37h 35m

Nassau Intl

Thu 5/7

6:30 pm-8:40 pm

2 stops32h 10m

$796

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 2/24

7:50 am-3:06 pm

2 stops25h 16m

San Juan Luis Munoz Marin Intl

Tue 3/3

7:10 am-3:17 pm

1 stop38h 07m

$797

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Thu 2/26

10:50 pm-4:50 pm

2 stops36h 00m

Oranjestad Reina Beatrix

Mon 3/2

3:00 pm-5:35 pm

2 stops32h 35m

$812

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 3/9

1:50 pm-2:45 pm

2 stops18h 55m

San Juan Luis Munoz Marin Intl

Tue 3/24

8:20 pm-2:25 pm

2 stops24h 05m

$821

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 2/24

9:30 pm-11:10 pm

2 stops19h 40m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:10 am-9:00 pm

2 stops20h 50m

$821

HonoluluPunta Cana

HNL - PUJ

HNLPUJ

Honolulu

Thu 3/5

6:45 pm-4:48 pm

1 stop16h 03m

Punta Cana

Mon 3/9

4:43 pm-11:14 am

2 stops24h 31m

$825

HonoluluPunta Cana

HNL - PUJ

HNLPUJ

Honolulu

Tue 4/21

6:34 pm-4:25 pm

1 stop15h 51m

Punta Cana

Sat 4/25

4:30 pm-12:23 pm

2 stops25h 53m

$825

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 3/9

8:10 pm-3:36 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Mon 3/23

1:05 am-2:33 pm

1 stop19h 28m

$836

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Tue 3/31

1:50 pm-1:15 pm

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Sun 4/5

9:50 pm-9:00 pm

2 stops29h 10m

$841

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 43 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, May is the cheapest month in which you can book a flight from Hawaii to Caribbean (average of $448). Flying from Hawaii to Caribbean 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. 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?

    United Airlines, Air Canada, and American Airlines can get you from Hawaii to Caribbean in just under 16h 03m. Your travel time can differ by up to 21h 32m. The distance between Hawaii and Caribbean is about 5728 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, May is the cheapest month in which you can book a flight from Hawaii to Caribbean (average of $448). Flying from Hawaii to Caribbean 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$412Average$1,010FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$516Average$1,245FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$755Average$1,004FlexibilityNo cancel feeOn-time71%

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