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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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Round-trip from

$765
(Delta)

One-way from

$395
(Air Canada)

Popular in

July

Cheapest in

August

Average price

$874
From Hawaii to Caribbean
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One-way flight from Hawaii to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($75 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 April 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 April 30, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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 11/55:40 pmHNL - SJU
1 stop17h 35mDelta
Wed 11/127:00 amSJU - HNL
2 stops20h 47mDelta
Deal found 4/28$755
This United Airlines deal was found by Cheapflights users on 4/28. 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 9/17:50 pmHNL - SJU
1 stop13h 52mUnited Airlines
Sat 9/61:05 amSJU - HNL
2 stops18h 15mUnited Airlines
Deal found 4/28$780
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 5/2611:15 amHNL - SJU
2 stops17h 05mSouthwest
Mon 6/95:50 pmSJU - HNL
2 stops22h 20mSouthwest
Deal found 4/27$795
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sun 6/225:33 pmHNL - SJU
2 stops18h 32mAmerican Airlines
Fri 6/278:00 amSJU - HNL
2 stops18h 52mAmerican Airlines
Deal found 4/28$815
This Booking.com deal was found by Cheapflights users on 4/28. 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.
Sun 8/1710:05 pmHNL - MBJ
2 stops32h 10mAir Canada
Wed 8/2012:10 pmMBJ - HNL
2 stops37h 40mAir Canada
Deal found 4/28$847
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 9/812:45 pmHNL - STI
2 stops17h 35mAmerican Airlines
Sat 9/201:35 pmSTI - HNL
2 stops27h 39mAmerican Airlines
Deal found 4/29$879
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 10/2112:43 pmHNL - PLS
2 stops19h 47mAmerican Airlines
Tue 10/283:30 pmPLS - HNL
2 stops27h 20mAmerican Airlines
Deal found 4/29$932
This JetBlue deal was found by Cheapflights users on 4/28. 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.
Sun 5/42:15 pmHNL - SJU
1 stop15h 49mJetBlue
Tue 5/273:33 amSJU - HNL
1 stop16h 07mJetBlue
Deal found 4/28$943
This American Airlines deal was found by Cheapflights users on 4/28. 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 9/145:00 pmSDQ - HNL
2 stops24h 14mAmerican Airlines
Deal found 4/28$964
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Thu 6/1210:05 pmHNL - MBJ
3 stops32h 37mMultiple Airlines
Thu 6/195:10 pmMBJ - HNL
3 stops32h 40mMultiple Airlines
Deal found 4/28$994
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sun 8/177:00 pmHNL - MBJ
1 stop14h 20mAmerican Airlines
Wed 8/204:35 pmMBJ - HNL
2 stops23h 51mAmerican Airlines
Deal found 4/28$1,010
This Delta deal was found by Cheapflights users on 4/28. 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 9/13:00 pmHNL - SDQ
1 stop16h 24mDelta
Sun 9/146:10 amSDQ - HNL
2 stops19h 40mDelta
Deal found 4/28$1,094

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 April 30, 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

Sun 8/24

3:45 pm-1:10 pm

1 stop15h 25m

San Juan Luis Munoz Marin Intl

Thu 9/4

7:00 am-9:20 pm

2 stops20h 20m

$765

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 9/1

7:50 pm-3:42 pm

1 stop13h 52m

San Juan Luis Munoz Marin Intl

Sat 9/6

1:05 am-1:20 pm

2 stops18h 15m

$780

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 5/26

11:15 am-10:20 am

2 stops17h 05m

San Juan Luis Munoz Marin Intl

Mon 6/9

5:50 pm-10:10 am

2 stops22h 20m

$795

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Sun 6/22

5:33 pm-11:25 pm

1 stop23h 52m

San Juan Luis Munoz Marin Intl

Fri 6/27

8:00 am-8:52 pm

2 stops18h 52m

$815

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Sun 8/17

10:05 pm-11:15 am

2 stops32h 10m

Montego Bay Sangster Intl

Wed 8/20

12:10 pm-8:50 pm

2 stops37h 40m

$847

HonoluluSantiago de los Caballeros

HNL - STI

HNLSTI

Honolulu

Mon 9/8

12:45 pm-12:20 pm

2 stops17h 35m

Santiago de los Caballeros

Sat 9/20

1:35 pm-11:14 am

2 stops27h 39m

$879

HonoluluSan Juan

HNL - SJU

HNLSJU

Honolulu

Mon 5/26

3:15 pm-12:44 pm

1 stop15h 29m

San Juan Luis Munoz Marin Intl

Sun 6/8

3:33 am-1:40 pm

1 stop16h 07m

$909

HonoluluProvidenciales

HNL - PLS

HNLPLS

Honolulu

Tue 10/21

12:43 pm-2:30 pm

2 stops19h 47m

Providenciales

Tue 10/28

3:30 pm-12:50 pm

2 stops27h 20m

$932

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

5:00 pm-11:14 am

2 stops24h 14m

$964

HonoluluMontego Bay

HNL - MBJ

HNLMBJ

Honolulu

Thu 6/12

10:05 pm-11:42 am

3 stops32h 37m

Montego Bay Sangster Intl

Thu 6/19

5:10 pm-8:50 pm

3 stops32h 40m

$994

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 29 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 December is currently the most expensive (average of $336). 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 April 30, 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 April 30, 2025.
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,402 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Air Canada, with whom users have recently found tickets for as low as $395. However, be on the lookout for offers from Southwest and Delta, 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 December is currently the most expensive (average of $336). 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 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$567Average$940FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$707Average$1,010FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$711Average$1,141FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$802Average$1,327FlexibilityNo cancel feeOn-time85%

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