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$415+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$751
(United Airlines)

One-way from

$415
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$1,094
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. 10% potential increase in price ($116 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/10. 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 9/58:00 amHNL - SJU
2 stops22h 00mUnited Airlines
Thu 9/181:05 amSJU - HNL
2 stops21h 24mUnited Airlines
Deal found 6/10$751
This Delta deal was found by Cheapflights users on 6/10. 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 11/58:55 pmHNL - SJU
2 stops20h 55mDelta
Wed 11/127:00 amSJU - HNL
2 stops19h 20mDelta
Deal found 6/10$785
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/53:40 pmHNL - NAS
2 stops42h 17mMultiple Airlines
Sat 11/155:55 pmNAS - HNL
2 stops47h 59mMultiple Airlines
Deal found 6/10$796
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:30 pmHNL - NAS
2 stops15h 40mAir Canada
Sat 11/159:10 pmNAS - HNL
2 stops29h 24mAir Canada
Deal found 6/11$807
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Sat 11/1511:59 pmHNL - PUJ
2 stops39h 30mMultiple Airlines
Fri 11/2111:00 amPUJ - HNL
1 stop40h 24mMultiple Airlines
Deal found 6/10$821
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/2511:04 pmHNL - SJU
2 stops18h 55mAmerican Airlines
Mon 9/86:10 amSJU - HNL
2 stops21h 22mAmerican Airlines
Deal found 6/11$825
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sun 7/611:00 amHNL - SJU
2 stops19h 35mSouthwest
Sun 7/139:05 pmSJU - HNL
2 stops23h 00mSouthwest
Deal found 6/11$875
This Delta deal was found by Cheapflights users on 6/10. 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 9/81:25 pmHNL - STI
2 stops17h 18mDelta
Sat 9/209:20 pmSTI - HNL
2 stops24h 51mDelta
Deal found 6/10$899
This American Airlines deal was found by Cheapflights users on 6/12. 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 9/110:00 pmHNL - SDQ
2 stops16h 30mAmerican Airlines
Sun 9/147:00 amSDQ - HNL
2 stops20h 32mAmerican Airlines
Deal found 6/12$904
This Delta deal was found by Cheapflights users on 6/10. 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 9/13:25 pmHNL - SDQ
1 stop15h 09mDelta
Sun 9/146:10 amSDQ - HNL
2 stops19h 40mDelta
Deal found 6/10$939
This United Airlines deal was found by Cheapflights users on 6/10. 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 6/247:00 amHNL - PUJ
2 stops26h 05mUnited Airlines
Fri 6/271:50 pmPUJ - HNL
2 stops31h 14mUnited Airlines
Deal found 6/10$989
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/183:10 pmHNL - SJU
1 stop15h 30mJetBlue
Mon 9/223:03 amSJU - HNL
1 stop16h 52mJetBlue
Deal found 6/12$989

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 12, 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

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Fri 9/5

8:00 am-12:00 pm

2 stops22h 00m

San Juan Luis Munoz Marin Intl

Thu 9/18

1:05 am-4:29 pm

2 stops21h 24m

$751

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Wed 11/5

8:55 pm-11:50 pm

2 stops20h 55m

San Juan Luis Munoz Marin Intl

Wed 11/12

7:00 am-8:20 pm

2 stops19h 20m

$785

HonoluluNassau

HNL - NAS

HNLNAS

Honolulu

Wed 11/5

3:40 pm-2:57 pm

2 stops42h 17m

Nassau Intl

Sat 11/15

5:55 pm-12:54 pm

2 stops47h 59m

$796

HonoluluNassau

HNL - NAS

HNLNAS

Honolulu

Wed 11/5

11:30 pm-8:10 pm

2 stops15h 40m

Nassau Intl

Sat 11/15

9:10 pm-9:34 pm

2 stops29h 24m

$807

HonoluluPunta Cana

HNL - PUJ

HNLPUJ

Honolulu

Sat 11/15

11:59 pm-9:29 pm

2 stops39h 30m

Punta Cana

Fri 11/21

11:00 am-9:24 pm

1 stop40h 24m

$821

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 8/25

11:04 pm-11:59 pm

2 stops18h 55m

San Juan Luis Munoz Marin Intl

Mon 9/8

6:10 am-9:32 pm

2 stops21h 22m

$825

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sun 7/6

11:00 am-12:35 pm

2 stops19h 35m

San Juan Luis Munoz Marin Intl

Sun 7/13

9:05 pm-2:05 pm

2 stops23h 00m

$875

HonoluluSantiago de los Caballeros

HNL - STI

HNLSTI

Honolulu

Mon 9/8

1:25 pm-12:43 pm

2 stops17h 18m

Santiago de los Caballeros

Sat 9/20

9:20 pm-4:11 pm

2 stops24h 51m

$899

HonoluluSanto Domingo

HNL - SDQ

HNLSDQ

Honolulu

Mon 9/1

10:00 pm-8:30 pm

2 stops16h 30m

Santo Domingo Las Americas

Sun 9/14

7:00 am-9:32 pm

2 stops20h 32m

$904

HonoluluSanto Domingo

HNL - SDQ

HNLSDQ

Honolulu

Mon 9/1

3:25 pm-12:34 pm

1 stop15h 09m

Santo Domingo Las Americas

Sun 9/14

6:10 am-7:50 pm

2 stops19h 40m

$939

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 35 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 June 12, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Copa Airlines
7.5
Good
1,451 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $436. However, be on the lookout for offers from Southwest 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, 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

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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 4 airlines flying from Hawaii to Caribbean

Discover the top 4 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$474Average$1,052FlexibilityNo cancel feeOn-time62%
DeltaCheapest$528Average$940FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$707Average$1,002FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$711Average$1,151FlexibilityNo cancel feeOn-time71%

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