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Caribbean

$395+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
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 June 24, 2026.

This Southwest deal was found by Cheapflights users on 6/23. 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 9/159:55 pm
HNL
-
SJU
2 stops18h 05m
Southwest
Mon 9/285:30 am
SJU
-
HNL
2 stops21h 50m
Southwest
Deal found 6/23$696
This Air Canada deal was found by Cheapflights users on 6/22. 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 10/271:00 pm
HNL
-
MBJ
2 stops17h 50m
Air Canada
Thu 10/2912:50 pm
MBJ
-
HNL
2 stops36h 43m
Air Canada
Deal found 6/22$704
This United Airlines deal was found by Cheapflights users on 6/23. 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 8/251:00 pm
LIH
-
SJU
2 stops19h 44m
United Airlines
Thu 8/274:55 pm
SJU
-
LIH
2 stops24h 45m
United Airlines
Deal found 6/23$769
This Southwest deal was found by Cheapflights users on 6/23. 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.
Fri 9/189:55 pm
HNL
-
SJU
2 stops18h 00m
Southwest
Mon 9/215:30 am
SJU
-
HNL
2 stops21h 50m
Southwest
Deal found 6/23$813
This Southwest deal was found by Cheapflights users on 6/23. 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 8/199:25 pm
HNL
-
SJU
2 stops19h 25m
Southwest
Tue 8/256:00 am
SJU
-
HNL
2 stops21h 20m
Southwest
Deal found 6/23$841
This United Airlines deal was found by Cheapflights users on 6/23. 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 8/208:00 pm
HNL
-
SJU
1 stop13h 42m
United Airlines
Sat 8/221:00 am
SJU
-
HNL
2 stops18h 28m
United Airlines
Deal found 6/23$866
This United Airlines deal was found by Cheapflights users on 6/22. 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 11/27:55 am
HNL
-
SJU
2 stops25h 45m
United Airlines
Fri 11/65:50 pm
SJU
-
HNL
2 stops24h 58m
United Airlines
Deal found 6/22$872
This American Airlines deal was found by Cheapflights users on 6/23. 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 8/710:00 pm
LIH
-
SJU
2 stops17h 55m
American Airlines
Fri 8/147:30 am
SJU
-
LIH
2 stops18h 39m
American Airlines
Deal found 6/23$886
This United Airlines deal was found by Cheapflights users on 6/22. 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 10/273:55 pm
HNL
-
MBJ
1 stop15h 53m
United Airlines
Thu 10/292:20 pm
MBJ
-
HNL
2 stops28h 07m
United Airlines
Deal found 6/22$892
This Delta deal was found by Cheapflights users on 6/23. 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.
Tue 9/153:10 pm
HNL
-
SJU
1 stop16h 37m
Delta
Mon 9/287:00 am
SJU
-
HNL
2 stops20h 13m
Delta
Deal found 6/23$901
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/277:50 pm
HNL
-
SJU
2 stops22h 00m
United Airlines
Thu 8/67:20 am
SJU
-
HNL
2 stops20h 18m
United Airlines
Deal found 6/20$906
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/1312:23 pm
HNL
-
AUA
2 stops20h 57m
American Airlines
Mon 7/202:34 pm
AUA
-
HNL
2 stops27h 37m
American Airlines
Deal found 6/21$916

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 June 24, 2026.

Round-trip from

$704
(Air Canada)

One-way from

$395
(Travelocity)

Popular in

December

Cheapest in

March

Average price

$1,197
From Hawaii to Caribbean
Search Deals
One-way flight from Hawaii to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($98 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 June 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 June 24, 2026.
Use the filters below to find and compare flights from Hawaii to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LihueSan Juan

LIH - SJU

LIHSJU

Lihue

Tue 8/25

1:00 pm-2:44 pm

2 stops19h 44m

San Juan Luis Munoz Marin Intl

Thu 8/27

4:55 pm-11:40 am

2 stops24h 45m

$769
Quickest round-trip

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Thu 8/20

8:30 pm-6:33 pm

2 stops16h 03m

San Juan Luis Munoz Marin Intl

Sun 8/23

7:30 am-8:10 pm

2 stops18h 40m

$866

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 9/18

8:00 pm-3:42 pm

1 stop13h 42m

San Juan Luis Munoz Marin Intl

Sun 9/20

1:00 am-4:21 pm

2 stops21h 21m

$866

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 11/2

7:55 am-3:40 pm

2 stops25h 45m

San Juan Luis Munoz Marin Intl

Fri 11/6

5:50 pm-12:48 pm

2 stops24h 58m

$872

LihueSan Juan

LIH - SJU

LIHSJU

Lihue

Fri 8/7

10:00 pm-9:55 pm

2 stops17h 55m

San Juan Luis Munoz Marin Intl

Fri 8/14

7:30 am-8:09 pm

2 stops18h 39m

$886

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Tue 10/27

3:55 pm-12:48 pm

1 stop15h 53m

Montego Bay Sangster Intl

Thu 10/29

2:20 pm-1:27 pm

2 stops28h 07m

$892

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Mon 7/13

12:23 pm-4:59 pm

2 stops22h 36m

Oranjestad Reina Beatrix

Mon 7/20

4:59 pm-12:11 pm

2 stops25h 12m

$916

LihueSan Juan

LIH - SJU

LIHSJU

Lihue

Mon 8/3

1:19 pm-2:12 pm

2 stops18h 53m

San Juan Luis Munoz Marin Intl

Mon 8/10

7:24 pm-2:55 pm

2 stops25h 31m

$919

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Tue 7/7

7:50 pm-1:30 pm

1 stop12h 40m

Montego Bay Sangster Intl

Thu 7/16

2:40 pm-9:40 am

2 stops24h 00m

$944

HonoluluOranjestad

HNL - AUA

HNLAUA

Honolulu

Mon 7/13

3:25 pm-12:40 pm

1 stop15h 15m

Oranjestad Reina Beatrix

Mon 7/20

1:50 pm-3:13 pm

2 stops31h 23m

$956

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 41 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Hawaii to Caribbean (average of $605). Flying from Hawaii to Caribbean in February is currently the most expensive (average of $954). 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 and American Airlines can get you from Hawaii to Caribbean in just under 16h 03m. Your travel time can differ by up to 1h 51m. The distance between Hawaii and Caribbean is about 5876 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $428. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Hawaii to Caribbean for a low price.

  • 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, April is the cheapest month in which you can book a flight from Hawaii to Caribbean (average of $605). Flying from Hawaii to Caribbean in February is currently the most expensive (average of $954). 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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$604Average$995FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$775Average$935FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$786Average$821FlexibilityNo cancel feeOn-time63%

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