$273 Find Cheap Flights from Gainesville to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gainesville to Caribbean departing on 2/14. 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
1 adult, Economy, 0 bags

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Cheap Flights from Gainesville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$615
Montego Bay
Montego Bay1 stop$572
Nassau
Nassau1 stop$496
Santiago de los Caballeros
Santiago de los Caballeros1 stop$554
Saint Thomas Island
Saint Thomas Island1 stop$500
Kingston
Kingston1 stop$644
Simpson Bay
Simpson Bay1 stop$567
St. John's
St. John's1 stop$648
Punta Cana
Punta Cana1 stop$615
Montego Bay
Montego Bay1 stop$572
Nassau
Nassau1 stop$496
Santiago de los Caballeros
Santiago de los Caballeros1 stop$554
Saint Thomas Island
Saint Thomas Island1 stop$500
Kingston
Kingston1 stop$644
Simpson Bay
Simpson Bay1 stop$567
St. John's
St. John's1 stop$648

Book Cheap Gainesville to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gainesville to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Gainesville to Caribbean

Fri, Mar 20 - Tue, Mar 31
American Airlines Logo
6:00 am - 8:50 pm
GNV
-
SJU
14h 50m
1 stop
American Airlines Logo
6:33 am - 11:00 pm
SJU
-
GNV
16h 27m
1 stop
$386American Airlines
Mon, Feb 23 - Mon, Mar 2
American Airlines Logo
7:10 am - 11:31 pm
GNV
-
SJU
15h 21m
1 stop
American Airlines Logo
7:01 pm - 11:59 pm
SJU
-
GNV
5h 58m
1 stop
$426American Airlines
Tue, Mar 31 - Tue, Apr 14
American Airlines Logo
7:49 am - 8:50 pm
GNV
-
SJU
13h 01m
2 stops
American Airlines Logo
5:45 am - 9:44 pm
SJU
-
GNV
15h 59m
2 stops
$456American Airlines
Mon, Jul 20 - Fri, Jul 24
American Airlines Logo
7:34 pm - 9:33 am
GNV
-
SJU
13h 59m
2 stops
American Airlines Logo
6:00 am - 10:37 pm
SJU
-
GNV
16h 37m
2 stops
$466American Airlines
Sun, May 10 - Thu, May 14
Delta Logo
6:00 am - 3:21 pm
GNV
-
STT
9h 21m
1 stop
Delta Logo
3:00 pm - 10:29 pm
STT
-
GNV
7h 29m
1 stop
$550Delta
Fri, Jun 26 - Tue, Jun 30
Delta Logo
6:00 am - 2:40 pm
GNV
-
PLS
8h 40m
1 stop
Delta Logo
4:05 pm - 10:29 pm
PLS
-
GNV
6h 24m
1 stop
$715Delta
Fri, Apr 10 - Tue, Apr 14
Delta Logo
6:00 am - 3:40 pm
GNV
-
PUJ
9h 40m
1 stop
Delta Logo
2:46 pm - 10:39 pm
PUJ
-
GNV
7h 53m
1 stop
$725Delta
Fri, Apr 10 - Tue, Apr 14
WestJet Logo
6:00 am - 8:57 am
GNV
-
PUJ
26h 57m
2 stops
WestJet Logo
3:30 pm - 4:09 pm
PUJ
-
GNV
24h 39m
2 stops
$1,977WestJet
Thu, Mar 12 - Thu, Mar 19
WestJet Logo
7:00 pm - 5:24 pm
GNV
-
MBJ
47h 24m
2 stops
WestJet Logo
1:55 pm - 4:08 pm
MBJ
-
GNV
25h 13m
2 stops
$2,012WestJet
Sun, Apr 12 - Fri, Apr 17
WestJet Logo
7:00 pm - 12:49 pm
GNV
-
MBJ
18h 49m
2 stops
WestJet Logo
1:55 pm - 1:16 pm
MBJ
-
GNV
22h 21m
2 stops
$2,097WestJet
Booking Insights

KAYAK's insights & trends for Gainesville to Caribbean flights

Get data-powered insights and trends into flights from Gainesville to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Gainesville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Gainesville to Caribbean were found on American Airlines ($386) and Delta ($426).

Find deals

Good to know

Low seasonNovember
Cheapest flight$273
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Gainesville to San Juan

FAQs - booking Caribbean flights

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

    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 Gainesville to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Gainesville to Caribbean 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 Gainesville to Caribbean?

    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 from Gainesville to Caribbean with an airline and back with another airline.

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

    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 from Gainesville to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Gainesville to Caribbean

 
Need help choosing which airline to fly with from Gainesville to Caribbean? 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.
7.2
American AirlinesOverall score based on 11201 reviews
8.0Crew
7.5Boarding
7.2Comfort
6.9Entertainment
6.4Food
Airline reviews

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

10.0 ExcellentRicciyah, Jan 2026
PBI - PHL
Read more American Airlines reviews

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Gainesville (GNV)