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Find cheap flights from Hawaii to Caribbean Islands from $298

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hawaii to Caribbean Islands departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 5/25
Sat 6/1

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Good to know

Low season

September

High season

December

Cheapest flight

$298
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Honolulu to Santiago de los Caballeros

FAQs for booking flights from Hawaii to Caribbean Islands

  • How does KAYAK find such low prices on flights from Hawaii to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean Islands with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean Islands from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Hawaii to Caribbean Islands

 
Need help choosing which airline to fly with from Hawaii to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.0
Cape AirOverall score based on 57 reviews
8.8food
9.5crew
8.4comfort
8.9boarding
9.1entertainment
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

No comments, the complete handling and flying was excellent,keep up the good works.

Book cheap flights from Hawaii to Caribbean Islands

Recent round-trip flight deals

8/22Thu
2 stopsAmerican Airlines
20h 26mHNL-SJU
9/2Mon
2 stopsAmerican Airlines
18h 27mSJU-HNL
$810
8/21Wed
1 stopAmerican Airlines
23h 22mHNL-SJU
9/3Tue
2 stopsAmerican Airlines
18h 27mSJU-HNL
$825
8/22Thu
2 stopsAmerican Airlines
18h 31mHNL-SJU
9/2Mon
2 stopsAmerican Airlines
18h 27mSJU-HNL
$830
8/21Wed
1 stopAmerican Airlines
23h 22mHNL-SJU
9/3Tue
2 stopsAmerican Airlines
18h 27mSJU-HNL
$846
6/14Fri
2 stopsAeromexico
28h 36mHNL-SDQ
6/25Tue
2 stopsAeromexico
40h 15mSDQ-HNL
$873
7/22Mon
2 stopsDelta
24h 55mHNL-MBJ
7/26Fri
2 stopsDelta
25h 37mMBJ-HNL
$912
7/15Mon
1 stopDelta
15h 57mHNL-SJU
7/31Wed
2 stopsDelta
18h 40mSJU-HNL
$919
7/1Mon
2 stopsCopa Airlines
35h 42mHNL-POS
7/15Mon
2 stopsCopa Airlines
21h 35mPOS-HNL
$1,165
7/18Thu
1 stopJetBlue
18h 39mHNL-SJU
7/25Thu
1 stopJetBlue
15h 54mSJU-HNL
$1,266
6/12Wed
1 stopJetBlue
17h 34mHNL-SJU
6/16Sun
1 stopJetBlue
15h 54mSJU-HNL
$1,273

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Recent one-way flight deals

5/9Thu
1 stopDelta
17h 54mHNL-STI
$298
10/15Tue
2 stopsCopa Airlines
23h 17mHNL-POS
$307
5/2Thu
2 stopsWestJet
36h 49mHNL-MBJ
$331
5/2Thu
3 stopsWestJet
36h 49mHNL-MBJ
$335
5/10Fri
2 stopsUnited Airlines
34h 37mHNL-STI
$380
5/22Wed
3 stops
32h 19mHNL-SJU
$452
7/1Mon
2 stopsUnited Airlines
19h 43mHNL-POS
$487
8/28Wed
2 stopsAmerican Airlines
18h 31mHNL-SJU
$522
5/22Wed
2 stopsAmerican Airlines
19h 05mHNL-SJU
$524
7/1Mon
3 stops
41h 20mHNL-POS
$625

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Last minute flights from Hawaii to Caribbean Islands

Last minute flight, train and bus deals

4/30Tue
multi-stopDelta
24h 34mHNL-SDQ
5/3Fri
multi-stopDelta
26h 29mSDQ-HNL
$970
4/30Tue
multi-stopDelta
16h 50mHNL-SDQ
5/3Fri
multi-stopDelta
26h 13mSDQ-HNL
$975
4/30Tue
multi-stopDelta
15h 52mHNL-SDQ
5/3Fri
multi-stopDelta
26h 29mSDQ-HNL
$1,010
4/30Tue
multi-stopDelta
24h 34mHNL-SDQ
5/3Fri
multi-stopDelta
29h 13mSDQ-HNL
$1,015

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Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - Hawaii

Cabin classes:

$362
$363
$352
$68

Browse origins:

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Browse destinations:

$1,023
Flights to Kingston, Caribbean Islands
$847
Flights to Montego Bay, Caribbean Islands
$846
Flights to Nassau, Caribbean Islands
$961
Flights to Oranjestad, Caribbean Islands
$930
Flights to Port Au Prince, Caribbean Islands
$1,124
Flights to Port of Spain, Caribbean Islands
$1,177
Flights to Providenciales, Caribbean Islands
$766
Flights to Punta Cana, Caribbean Islands
$694
Flights to Santiago de los Caballeros, Caribbean Islands
$873
Flights to Santo Domingo, Caribbean Islands
View more