$273 Find Cheap Flights from Gainesville to Caribbean - Compare and Save

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 7/21. 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$596
Montego Bay
Montego Bay1 stop$489
Nassau
Nassau1 stop$606
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$707
St. John's
St. John's2 stops$760
Punta Cana
Punta Cana1 stop$596
Montego Bay
Montego Bay1 stop$489
Nassau
Nassau1 stop$606
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$707
St. John's
St. John's2 stops$760

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, Aug 7 - Fri, Aug 14
American Airlines Logo
6:15 am - 1:49 pm
GNV
-
MBJ
8h 34m
1 stop
American Airlines Logo
2:37 pm - 10:09 am
MBJ
-
GNV
18h 32m
1 stop
$489American Airlines
Fri, Aug 7 - Fri, Aug 14
American Airlines Logo
6:39 pm - 11:42 am
GNV
-
MBJ
18h 03m
2 stops
American Airlines Logo
2:37 pm - 10:09 am
MBJ
-
GNV
18h 32m
1 stop
$494American Airlines
Fri, Aug 7 - Fri, Aug 14
American Airlines Logo
6:39 pm - 1:49 pm
GNV
-
MBJ
20h 10m
2 stops
American Airlines Logo
5:08 pm - 10:09 am
MBJ
-
GNV
16h 01m
2 stops
$537American Airlines
Sun, Aug 9 - Sun, Aug 16
Delta Logo
6:00 am - 11:46 am
GNV
-
SJU
5h 46m
1 stop
Delta Logo
7:00 am - 12:48 pm
SJU
-
GNV
5h 48m
1 stop
$541Delta
Sun, Aug 9 - Sun, Aug 16
American Airlines Logo
5:45 am - 1:34 pm
GNV
-
MBJ
8h 49m
1 stop
American Airlines Logo
12:38 pm - 10:09 am
MBJ
-
GNV
20h 31m
1 stop
$555American Airlines
Tue, Jul 21 - Sat, Jul 25
Delta Logo
3:41 pm - 10:30 pm
GNV
-
SJU
6h 49m
1 stop
Delta Logo
6:05 am - 4:39 pm
SJU
-
GNV
10h 34m
1 stop
$581Delta
Wed, Jul 8 - Sat, Jul 11
Delta Logo
6:33 am - 3:34 pm
GNV
-
MBJ
10h 01m
1 stop
Delta Logo
4:59 pm - 9:28 am
MBJ
-
GNV
15h 29m
1 stop
$584Delta
Wed, Aug 12 - Sun, Aug 16
WestJet Logo
7:01 pm - 11:10 am
GNV
-
NAS
40h 09m
2 stops
WestJet Logo
12:00 pm - 12:23 pm
NAS
-
GNV
24h 23m
2 stops
$1,595WestJet
Tue, Dec 8 - Thu, Dec 10
WestJet Logo
7:05 pm - 3:40 pm
GNV
-
NAS
20h 35m
2 stops
WestJet Logo
11:20 am - 10:27 pm
NAS
-
GNV
35h 07m
2 stops
$1,627WestJet
Tue, Dec 8 - Thu, Dec 10
WestJet Logo
10:20 am - 3:40 pm
GNV
-
NAS
29h 20m
2 stops
WestJet Logo
11:20 am - 12:22 pm
NAS
-
GNV
25h 02m
2 stops
$1,629WestJet
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.

What is the cheapest month to fly from Gainesville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gainesville to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Gainesville to Caribbean is September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are May and March, when the average cost of round-trip tickets is $1,279 and $1,060 respectively.

Good to know

Low seasonJune
Cheapest flight$273
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly and prices are also 3% 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.
7.1
American AirlinesOverall score based on 11757 reviews
7.2Comfort
6.4Food
7.9Crew
6.8Entertainment
7.5Boarding
Airline reviews

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

2.0 MediocreRachel, Jun 2026
MIA - UIO
Read more American Airlines reviews

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports