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Kailua-Kona

$786+ Cheap flights from Caribbean to Kailua-Kona (KOA)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — KOA
Mar 9 — Mar 161
Mon 3/9
Mon 3/16
1 adult, Economy
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Cheap flight deals from Caribbean to Kailua-Kona

Cheapest flights from Caribbean to Kailua-Kona
Explore the most affordable flight options available from Caribbean to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 7, 2026.

This Southwest deal was found by Cheapflights users on 2/5. 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 4/278:40 pm
SJU
-
KOA
2 stops22h 35m
Southwest
Thu 4/308:25 pm
KOA
-
SJU
2 stops21h 15m
Southwest
Deal found 2/5$786
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/237:40 am
SJU
-
KOA
2 stops35h 19m
United Airlines
Wed 2/258:55 pm
KOA
-
SJU
2 stops18h 05m
United Airlines
Deal found 2/2$896
This United Airlines deal was found by Cheapflights users on 2/5. 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.
Sun 4/261:00 am
SJU
-
KOA
2 stops20h 30m
United Airlines
Thu 4/3011:04 pm
KOA
-
SJU
3 stops36h 34m
United Airlines
Deal found 2/5$1,008
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/262:53 pm
SDQ
-
KOA
2 stops28h 00m
United Airlines
Mon 3/210:55 pm
KOA
-
SDQ
2 stops18h 51m
United Airlines
Deal found 2/2$1,100
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/264:00 pm
STI
-
KOA
2 stops30h 34m
United Airlines
Mon 3/22:08 pm
KOA
-
STI
3 stops27h 43m
United Airlines
Deal found 2/2$1,122
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/203:19 pm
SDQ
-
KOA
2 stops30h 55m
American Airlines
Sat 2/2810:40 pm
KOA
-
SDQ
2 stops19h 13m
American Airlines
Deal found 2/3$1,173
This United Airlines deal was found by Cheapflights users on 2/5. 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.
Sat 3/76:00 am
SDQ
-
KOA
2 stops36h 08m
United Airlines
Sat 3/146:56 pm
KOA
-
SDQ
2 stops35h 45m
United Airlines
Deal found 2/5$1,185
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/206:00 am
SDQ
-
KOA
2 stops36h 59m
United Airlines
Sat 2/281:58 pm
KOA
-
SDQ
3 stops27h 48m
United Airlines
Deal found 2/3$1,275
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Sat 3/215:50 pm
SDQ
-
KOA
2 stops27h 24m
American Airlines
Sat 3/285:30 pm
KOA
-
SDQ
2 stops23h 23m
American Airlines
Deal found 2/4$1,430
This American Airlines deal was found by Cheapflights users on 2/4. 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 7/912:39 am
SJU
-
KOA
2 stops19h 23m
American Airlines
Sun 7/199:45 pm
KOA
-
SJU
2 stops24h 47m
American Airlines
Deal found 2/4$3,213
This United Airlines deal was found by Cheapflights users on 2/4. 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 7/104:55 pm
SJU
-
KOA
3 stops25h 42m
United Airlines
Sun 7/1911:55 am
KOA
-
SJU
2 stops23h 43m
United Airlines
Deal found 2/4$3,578

Find flight deals from Caribbean to Kailua-Kona

Keep the following information in mind while searching for Caribbean to Kailua-Kona flight deals. Data was last updated February 7, 2026.

Round-trip from

$786
(Southwest)
From Caribbean to Kona Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Kailua-Kona 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 February 7, 2026.
Use the filters below to find and compare flights from Caribbean to Kailua-Kona that are best for you.

Fly from

Caribbean

Fly to

Kailua-Kona

Route

Depart

Return

Price

San JuanKailua-Kona

SJU - KOA

SJUKOA

San Juan Luis Munoz Marin Intl

Mon 4/27

8:40 pm-1:15 pm

2 stops22h 35m

Kona Intl

Thu 4/30

8:25 pm-11:40 pm

2 stops21h 15m

$786

San JuanKailua-Kona

SJU - KOA

SJUKOA

San Juan Luis Munoz Marin Intl

Mon 2/23

7:40 am-12:59 pm

2 stops35h 19m

Kona Intl

Wed 2/25

8:55 pm-9:00 pm

2 stops18h 05m

$896

San JuanKailua-Kona

SJU - KOA

SJUKOA

San Juan Luis Munoz Marin Intl

Sun 4/26

1:00 am-3:30 pm

2 stops20h 30m

Kona Intl

Thu 4/30

11:04 pm-5:38 pm

3 stops36h 34m

$1,008

Santo DomingoKailua-Kona

SDQ - KOA

SDQKOA

Santo Domingo Las Americas

Thu 2/26

2:53 pm-12:53 pm

2 stops28h 00m

Kona Intl

Mon 3/2

10:55 pm-11:46 pm

2 stops18h 51m

$1,100

Santiago de los CaballerosKailua-Kona

STI - KOA

STIKOA

Santiago de los Caballeros

Thu 2/26

4:00 pm-4:34 pm

2 stops30h 34m

Kona Intl

Mon 3/2

2:35 pm-11:51 pm

2 stops27h 16m

$1,122

Santo DomingoKailua-Kona

SDQ - KOA

SDQKOA

Santo Domingo Las Americas

Fri 2/20

3:19 pm-4:14 pm

2 stops30h 55m

Kona Intl

Sat 2/28

10:40 pm-11:53 pm

2 stops19h 13m

$1,173

Santo DomingoKailua-Kona

SDQ - KOA

SDQKOA

Santo Domingo Las Americas

Sat 3/7

6:00 am-12:08 pm

2 stops36h 08m

Kona Intl

Sat 3/14

6:56 pm-12:41 pm

2 stops35h 45m

$1,185

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Best time to book a flight from Caribbean to Kailua-Kona

Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona from Caribbean 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 Caribbean to Kailua-Kona
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Kailua-Kona. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Kailua-Kona from Caribbean?

    Most people fly into Kona Intl (KOA) if they book a flight to Kailua-Kona from Caribbean. Kona Intl is conveniently located just 7.7 mi from Kailua-Kona’s city center.

  • How long is the flight from Caribbean to Kailua-Kona?

    Airlines like Southwest and United Airlines fly from Caribbean to Kailua-Kona in about 22h 35m. The time it takes to get you to your destination can typically vary by up to 12h 44m. The distance between Caribbean and Kailua-Kona is about 5793 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Caribbean to Kailua-Kona?

    While some choose either Santiago de los Caballeros - Kona Intl or San Juan Luis Munoz Marin Intl - Kona Intl, Santo Domingo Las Americas - Kona Intl is the most popular route from Caribbean to Kailua-Kona.

  • Can I find deals for flights from Caribbean to Kailua-Kona that include hotel bookings?

    Yes. In addition to deals on Caribbean to Kailua-Kona flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Kailua-Kona?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Kailua-Kona.

  • Can I find deals for business class flights from Caribbean to Kailua-Kona?

    Yes. Cheapflights offers flight deals from Caribbean to Kailua-Kona by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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