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Caribbean Islands

$343+ Cheap flights from Gainesville (GNV) to Caribbean Islands

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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — SJU
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Gainesville to Caribbean Islands

Cheapest flights from Gainesville to Caribbean Islands
Explore the most affordable flight options available from Gainesville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2026.

This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:49 pm
GNV
-
SJU
2 stops14h 24m
American Airlines
Tue 4/281:31 pm
SJU
-
GNV
1 stop10h 28m
American Airlines
Deal found 2/20$396
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:47 pm
GNV
-
SJU
2 stops15h 26m
American Airlines
Sat 5/166:02 pm
SJU
-
GNV
1 stop5h 57m
American Airlines
Deal found 2/20$421
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
GNV
-
SJU
1 stop4h 53m
American Airlines
Sun 5/246:00 am
SJU
-
GNV
2 stops16h 38m
American Airlines
Deal found 2/20$426
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/76:00 am
GNV
-
SJU
1 stop4h 53m
American Airlines
Sun 5/106:45 am
SJU
-
GNV
1 stop16h 04m
American Airlines
Deal found 2/18$436
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/187:59 pm
GNV
-
SJU
2 stops14h 54m
American Airlines
Sat 4/255:45 am
SJU
-
GNV
2 stops11h 32m
American Airlines
Deal found 2/19$461
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/226:00 am
GNV
-
STX
1 stop14h 41m
American Airlines
Sun 5/318:08 am
STX
-
GNV
2 stops24h 54m
American Airlines
Deal found 2/18$480
This American Airlines deal was found by Cheapflights users on 2/17. 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 3/276:00 am
GNV
-
SJU
1 stop11h 11m
American Airlines
Mon 3/3011:46 am
SJU
-
GNV
1 stop12h 13m
American Airlines
Deal found 2/17$506
This American Airlines deal was found by Cheapflights users on 2/17. 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 5/237:32 pm
GNV
-
STT
1 stop15h 31m
American Airlines
Wed 5/274:48 pm
STT
-
GNV
1 stop7h 11m
American Airlines
Deal found 2/17$510
This American Airlines deal was found by Cheapflights users on 2/17. 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 11/86:00 am
GNV
-
PUJ
1 stop4h 55m
American Airlines
Fri 11/135:33 pm
PUJ
-
GNV
1 stop7h 17m
American Airlines
Deal found 2/17$525
This Delta deal was found by Cheapflights users on 2/17. 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 11/106:00 am
GNV
-
PUJ
1 stop8h 40m
Delta
Thu 11/122:55 pm
PUJ
-
GNV
2 stops19h 29m
Delta
Deal found 2/17$529
This Delta deal was found by Cheapflights users on 2/19. 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.
Sun 5/316:40 am
GNV
-
SJU
1 stop9h 35m
Delta
Sun 6/76:15 am
SJU
-
GNV
1 stop9h 51m
Delta
Deal found 2/19$531
This American Airlines deal was found by Cheapflights users on 2/16. 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 3/176:00 am
GNV
-
SJU
1 stop14h 50m
American Airlines
Thu 3/197:11 am
SJU
-
GNV
1 stop13h 13m
American Airlines
Deal found 2/16$546

Find flight deals from Gainesville to Caribbean Islands

Keep the following information in mind while searching for Gainesville to Caribbean Islands flight deals. Data was last updated February 20, 2026.

Round-trip from

$396
(American Airlines)

One-way from

$343
(Delta)

Popular in

July

Cheapest in

March

Average price

$390
From Gainesville Regional to Caribbean Islands
Search Deals
One-way flight from Gainesville Regional to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gainesville to Caribbean Islands 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 20, 2026.
Use the filters below to find and compare flights from Gainesville to Caribbean Islands that are best for you.

Fly from

Gainesville

Fly to

Caribbean Islands

Route

Depart

Return

Price

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Thu 8/6

6:00 am-3:59 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Tue 8/11

10:32 am-10:53 pm

1 stop12h 21m

$396

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Tue 4/21

6:49 pm-9:13 am

2 stops14h 24m

San Juan Luis Munoz Marin Intl

Tue 4/28

11:43 am-11:59 pm

1 stop12h 16m

$396

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Sat 5/9

7:59 pm-10:48 am

1 stop14h 49m

San Juan Luis Munoz Marin Intl

Sat 5/16

11:43 am-11:59 pm

1 stop12h 16m

$421

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Sat 4/18

7:59 pm-10:53 am

2 stops14h 54m

San Juan Luis Munoz Marin Intl

Sat 4/25

5:45 am-5:17 pm

2 stops11h 32m

$421

GainesvilleChristiansted

GNV - STX

GNVSTX

Gainesville Regional

Fri 5/22

6:00 am-8:41 pm

1 stop14h 41m

Christiansted Henry Rohlsen

Sun 5/31

8:08 am-9:02 am

2 stops24h 54m

$480

GainesvilleSaint Thomas Island

GNV - STT

GNVSTT

Gainesville Regional

Sat 5/23

7:32 pm-11:03 am

1 stop15h 31m

Saint Thomas Island Cyril E King

Wed 5/27

4:48 pm-1:24 pm

2 stops20h 36m

$510

GainesvilleChristiansted

GNV - STX

GNVSTX

Gainesville Regional

Tue 4/28

6:25 am-1:15 pm

1 stop6h 50m

Christiansted Henry Rohlsen

Sun 5/3

5:14 pm-11:59 pm

1 stop6h 45m

$586

GainesvilleChristiansted

GNV - STX

GNVSTX

Gainesville Regional

Wed 4/29

6:00 am-1:15 pm

1 stop7h 15m

Christiansted Henry Rohlsen

Sun 5/3

5:14 pm-11:59 pm

1 stop6h 45m

$586

GainesvilleChristiansted

GNV - STX

GNVSTX

Gainesville Regional

Thu 4/30

7:59 pm-4:13 pm

2 stops20h 14m

Christiansted Henry Rohlsen

Sun 5/3

5:14 pm-11:59 pm

1 stop6h 45m

$590

GainesvilleChristiansted

GNV - STX

GNVSTX

Gainesville Regional

Tue 4/28

6:25 am-4:13 pm

1 stop9h 48m

Christiansted Henry Rohlsen

Mon 5/4

5:14 pm-6:23 pm

2 stops25h 09m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 33 results
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Best time to book a flight from Gainesville to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Gainesville 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 Gainesville to Caribbean Islands

What is the cheapest month to book a flight from Gainesville to Caribbean Islands?

Currently, March is the cheapest month in which you can book a flight from Gainesville to Caribbean Islands (average of $78). Flying from Gainesville to Caribbean Islands in July is currently the most expensive (average of $119). 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.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 20, 2026.
Read through reviews of airlines operating flights from Gainesville to Caribbean Islands, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,321 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,321 reviews
American Airlines
7.2
Good
11,321 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

Find useful and relevant information for your journey from Gainesville to Caribbean Islands. 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 from for flights from Gainesville to Caribbean Islands?

    Located just 4.2 mi from the city center, Gainesville Regional (GNV) is the airport most travelers will use when flying to Caribbean Islands from Gainesville.

  • How long is the flight from Gainesville to Caribbean Islands?

    A quick flight from Gainesville to Caribbean Islands can take about 14h 24m. American Airlines provides one of the quickest options available for as low as $396. Gainesville and Caribbean Islands are separated by a distance of 1284 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Gainesville to Caribbean Islands?

    When deciding which route to take from Gainesville to Caribbean Islands consider Gainesville Regional - San Juan Luis Munoz Marin Intl, Gainesville Regional - Saint Thomas Island Cyril E King or Gainesville Regional - Oranjestad Reina Beatrix as they are the most popular.

  • Can I find deals for flights from Gainesville to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Gainesville to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Gainesville to Caribbean Islands?

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

  • Can I find deals for business class flights from Gainesville to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Gainesville to Caribbean Islands 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 Gainesville to Caribbean Islands?

    Currently, March is the cheapest month in which you can book a flight from Gainesville to Caribbean Islands (average of $78). Flying from Gainesville to Caribbean Islands in July is currently the most expensive (average of $119). 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.

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Top airline flying from Gainesville to Caribbean Islands

Discover the top airline that operate flights from Gainesville to Caribbean Islands. 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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$390Average$582FlexibilityNo cancel feeOn-time71%

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