$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 7/28. 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$1,172
Nassau
Nassau1 stop$571
Simpson Bay
Simpson Bay1 stop$702
Punta Cana
Punta Cana1 stop$1,172
Nassau
Nassau1 stop$571
Simpson Bay
Simpson Bay1 stop$702

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

Thu, Jun 18 - Wed, Jun 24
American Airlines Logo
6:30 am - 9:58 pm
GNV
-
SJU
15h 28m
1 stop
American Airlines Logo
10:29 am - 11:59 pm
SJU
-
GNV
13h 30m
1 stop
$486American Airlines
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
7:32 pm - 9:39 am
GNV
-
SJU
14h 07m
2 stops
American Airlines Logo
11:56 am - 11:59 pm
SJU
-
GNV
12h 03m
1 stop
$506American Airlines
Sat, Jul 11 - Tue, Jul 14
American Airlines Logo
7:00 am - 10:33 pm
GNV
-
SJU
15h 33m
1 stop
American Airlines Logo
7:14 pm - 11:59 pm
SJU
-
GNV
4h 45m
1 stop
$521American Airlines
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
7:32 pm - 9:39 am
GNV
-
SJU
14h 07m
2 stops
American Airlines Logo
11:56 am - 11:59 pm
SJU
-
GNV
12h 03m
1 stop
$526American Airlines
Sat, Aug 15 - Sat, Aug 29
Delta Logo
6:40 am - 2:10 pm
GNV
-
AUA
7h 30m
1 stop
Delta Logo
1:35 pm - 9:33 pm
AUA
-
GNV
7h 58m
1 stop
$813Delta
Sun, Aug 16 - Sat, Aug 29
Delta Logo
6:10 am - 2:10 pm
GNV
-
AUA
8h 00m
1 stop
Delta Logo
1:35 pm - 9:33 pm
AUA
-
GNV
7h 58m
1 stop
$892Delta
Sat, Jun 27 - Wed, Jul 1
Delta Logo
7:00 am - 2:35 pm
GNV
-
PUJ
7h 35m
1 stop
Delta Logo
4:00 pm - 10:50 pm
PUJ
-
GNV
6h 50m
1 stop
$1,172Delta
Sat, Jun 20 - Sat, Jun 27
WestJet Logo
10:17 am - 11:10 am
GNV
-
NAS
24h 53m
2 stops
WestJet Logo
12:00 pm - 9:30 am
NAS
-
GNV
21h 30m
2 stops
$1,609WestJet
Sun, Nov 1 - Thu, Nov 5
WestJet Logo
7:05 pm - 3:21 pm
GNV
-
SXM
19h 16m
2 stops
WestJet Logo
4:20 pm - 9:24 am
SXM
-
GNV
42h 04m
2 stops
$3,719WestJet
Sun, Nov 1 - Thu, Nov 5
WestJet Logo
6:00 am - 3:21 pm
GNV
-
SXM
32h 21m
2 stops
WestJet Logo
4:20 pm - 9:24 am
SXM
-
GNV
42h 04m
2 stops
$3,778WestJet
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 June, when tickets cost $0 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $1,060 and $600 respectively.

Good to know

Low seasonJune
Cheapest flight$273
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 17% 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 11641 reviews
7.9Crew
6.4Food
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

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.

8.0 ExcellentAnonymous, May 2026
RSW - ORD
Read more American Airlines reviews

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.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports