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Caribbean Islands

$283+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$405
(American Airlines)

One-way from

$283
(American Airlines)

Popular in

September

Cheapest in

March

Average price

$933
From Gainesville Regional to Caribbean Islands
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One-way flight from Gainesville Regional to Caribbean Islands
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Highest demand for flights based on searches. 19% potential increase in price ($129 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:00 amGNV - SJU
1 stop5h 06mAmerican Airlines
Tue 10/215:00 pmSJU - GNV
2 stops17h 09mAmerican Airlines
Deal found 9/14$405
This American Airlines deal was found by Cheapflights users on 9/13. 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 12/74:13 pmGNV - SJU
1 stop12h 16mAmerican Airlines
Sat 12/133:12 pmSJU - GNV
1 stop8h 23mAmerican Airlines
Deal found 9/13$430
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/137:44 pmGNV - SJU
2 stops15h 22mAmerican Airlines
Mon 10/207:10 amSJU - GNV
1 stop17h 07mAmerican Airlines
Deal found 9/15$465
This Delta deal was found by Cheapflights users on 9/13. 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 12/306:00 amGNV - NAS
1 stop5h 09mDelta
Wed 12/313:56 pmNAS - GNV
1 stop4h 47mDelta
Deal found 9/13$475
This Delta deal was found by Cheapflights users on 9/13. 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 12/296:00 amGNV - NAS
1 stop5h 09mDelta
Wed 12/313:56 pmNAS - GNV
1 stop4h 47mDelta
Deal found 9/13$490
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/14:46 pmGNV - PUJ
2 stops19h 10mAmerican Airlines
Wed 11/55:30 pmPUJ - GNV
2 stops18h 20mAmerican Airlines
Deal found 9/15$505
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/156:00 amGNV - SJU
1 stop6h 44mAmerican Airlines
Mon 10/207:00 pmSJU - GNV
1 stop4h 55mAmerican Airlines
Deal found 9/13$515
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/238:02 pmGNV - NAS
1 stop16h 10mAmerican Airlines
Sat 12/276:45 pmNAS - GNV
1 stop5h 14mAmerican Airlines
Deal found 9/14$522
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/306:00 amGNV - PUJ
1 stop5h 35mAmerican Airlines
Thu 11/62:37 pmPUJ - GNV
1 stop8h 49mAmerican Airlines
Deal found 9/15$524
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/296:13 amGNV - SJU
1 stop8h 40mAmerican Airlines
Fri 10/33:55 pmSJU - GNV
2 stops18h 26mAmerican Airlines
Deal found 9/14$525
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/44:43 pmGNV - NAS
2 stops18h 27mAmerican Airlines
Wed 10/810:55 amNAS - GNV
2 stops12h 31mAmerican Airlines
Deal found 9/14$539
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/16:00 amGNV - AUA
1 stop9h 50mAmerican Airlines
Sun 12/75:55 pmAUA - GNV
1 stop7h 03mAmerican Airlines
Deal found 9/14$565

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 September 15, 2025.
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

Fri 10/24

6:00 am-6:10 pm

1 stop12h 10m

San Juan Luis Munoz Marin Intl

Mon 10/27

7:00 pm-10:09 am

2 stops15h 09m

$405

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Tue 10/14

6:00 am-11:06 am

1 stop5h 06m

San Juan Luis Munoz Marin Intl

Tue 10/21

1:35 pm-11:55 pm

1 stop10h 20m

$405

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Mon 10/13

7:44 pm-12:44 pm

2 stops17h 00m

San Juan Luis Munoz Marin Intl

Mon 10/20

7:00 pm-10:09 am

2 stops15h 09m

$405

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Wed 10/15

6:00 am-12:44 pm

1 stop6h 44m

San Juan Luis Munoz Marin Intl

Mon 10/20

7:00 pm-10:09 am

2 stops15h 09m

$405

GainesvilleSan Juan

GNV - SJU

GNVSJU

Gainesville Regional

Sun 12/7

4:13 pm-5:29 am

1 stop12h 16m

San Juan Luis Munoz Marin Intl

Sat 12/13

3:12 pm-10:35 pm

1 stop8h 23m

$430

GainesvilleNassau

GNV - NAS

GNVNAS

Gainesville Regional

Tue 12/30

6:00 am-11:09 am

1 stop5h 09m

Nassau Intl

Wed 12/31

3:56 pm-8:43 pm

1 stop4h 47m

$475

GainesvilleNassau

GNV - NAS

GNVNAS

Gainesville Regional

Mon 12/29

6:00 am-11:09 am

1 stop5h 09m

Nassau Intl

Wed 12/31

3:56 pm-8:43 pm

1 stop4h 47m

$490

GainesvillePunta Cana

GNV - PUJ

GNVPUJ

Gainesville Regional

Sat 11/1

4:46 pm-11:56 am

2 stops19h 10m

Punta Cana

Wed 11/5

5:30 pm-10:50 am

2 stops18h 20m

$505

GainesvillePunta Cana

GNV - PUJ

GNVPUJ

Gainesville Regional

Thu 10/30

6:00 am-11:35 am

1 stop5h 35m

Punta Cana

Thu 11/6

2:37 pm-10:26 pm

1 stop8h 49m

$524

GainesvilleNassau

GNV - NAS

GNVNAS

Gainesville Regional

Tue 12/23

8:02 pm-11:18 am

2 stops15h 16m

Nassau Intl

Sat 12/27

4:39 pm-11:59 pm

1 stop7h 20m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, September is the cheapest month in which you can book a flight from Gainesville to Caribbean Islands (average of $254). Flying from Gainesville to Caribbean Islands 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 GNV to EPX?

Find hourly flight availability from Gainesville to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Gainesville to Caribbean Islands as you normally would.

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 September 15, 2025.
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
10,000 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 5h 09m. American Airlines provides one of the quickest options available for as low as $475. Gainesville and Caribbean Islands are separated by a distance of 435 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 - Oranjestad Reina Beatrix or Gainesville Regional - Nassau Intl 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, September is the cheapest month in which you can book a flight from Gainesville to Caribbean Islands (average of $254). Flying from Gainesville to Caribbean Islands 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.

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Top 2 airlines flying from Gainesville to Caribbean Islands

Discover the top 2 airlines 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$334Average$581FlexibilityNo cancel feeOn-time71%
DeltaCheapest$360Average$430FlexibilityNo cancel feeOn-timeN/A

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