$278 Find Cheap Flights from Gainesville to Caribbean Islands

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 Islands departing on 2/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gainesville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gainesville to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Gainesville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$508
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$505
Saint Thomas Island
Saint Thomas Island2 stops$539
Bridgetown
Bridgetown1 stop$596
St. John's
St. John's1 stop$650
Punta Cana
Punta Cana1 stop$508
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$505
Saint Thomas Island
Saint Thomas Island2 stops$539
Bridgetown
Bridgetown1 stop$596
St. John's
St. John's1 stop$650

Book Cheap Gainesville to Caribbean Islands 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 Islands 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 Islands

Wed, Apr 22 - Wed, Sep 30
American Airlines Logo
6:37 am - 2:35 pm
GNV
-
SJU
7h 58m1 stop
American Airlines Logo
2:05 pm - 11:43 pm
SJU
-
GNV
9h 38m1 stop
$365American Airlines
Wed, Apr 22 - Wed, Sep 30
American Airlines Logo
6:43 am - 2:35 pm
GNV
-
SJU
7h 52m2 stops
American Airlines Logo
12:05 pm - 8:49 am
SJU
-
GNV
20h 44m2 stops
$405American Airlines
Sun, Feb 15 - Sun, Feb 22
American Airlines Logo
6:00 am - 6:08 pm
GNV
-
SJU
11h 08m1 stop
American Airlines Logo
7:00 am - 11:57 pm
SJU
-
GNV
17h 57m1 stop
$424American Airlines
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
6:00 am - 12:30 pm
GNV
-
SJU
5h 30m1 stop
American Airlines Logo
7:12 pm - 11:57 pm
SJU
-
GNV
5h 45m1 stop
$485American Airlines
Sun, Jan 11 - Fri, Jan 16
American Airlines Logo
6:35 am - 1:22 pm
GNV
-
NAS
6h 47m1 stop
American Airlines Logo
11:58 am - 11:57 pm
NAS
-
GNV
11h 59m1 stop
$505American Airlines
Mon, Jan 26 - Sun, Feb 1
Delta Logo
6:00 am - 3:20 pm
GNV
-
BGI
8h 20m1 stop
Delta Logo
4:30 pm - 9:24 am
BGI
-
GNV
17h 54m1 stop
$596Delta
Fri, Jan 16 - Sun, Jan 18
Delta Logo
6:27 pm - 12:30 pm
GNV
-
AUA
17h 03m1 stop
Delta Logo
4:35 pm - 10:29 pm
AUA
-
GNV
6h 54m1 stop
$671Delta
Fri, Jan 16 - Sun, Jan 18
Delta Logo
6:27 pm - 1:55 pm
GNV
-
AUA
18h 28m2 stops
Delta Logo
4:35 pm - 10:29 pm
AUA
-
GNV
6h 54m1 stop
$675Delta
Fri, Jan 16 - Mon, Jan 19
WestJet Logo
10:11 am - 1:54 pm
GNV
-
MBJ
27h 43m2 stops
WestJet Logo
7:25 pm - 6:10 pm
MBJ
-
GNV
22h 45m2 stops
$1,659WestJet
Sat, Jan 17 - Mon, Jan 19
WestJet Logo
10:11 am - 3:40 pm
GNV
-
AUA
28h 29m2 stops
WestJet Logo
4:30 pm - 12:26 pm
AUA
-
GNV
20h 56m2 stops
$3,672WestJet
Booking Insights

KAYAK's insights & trends for Gainesville to Caribbean Islands flights

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

Can I save money by flying with a layover from Gainesville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $426, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Gainesville to Caribbean Islands?

The average price of all round-trip flights from Gainesville to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Gainesville to Caribbean Islands, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Caribbean Islands back to Gainesville, the best deals are generally found on Friday, with Wednesday being the most expensive.

Find deals

Good to know

Most popular time to fly and prices are also 6% lower on average.

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

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

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $373 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $500.

Reviews of the top airline flying from Gainesville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Gainesville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Gainesville to Caribbean Islands? 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 11048 reviews
6.5Food
6.9Entertainment
8.0Crew
7.2Comfort
7.5Boarding
Airline reviews

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.

8.0 ExcellentJolene, Dec 2025
GNV - DFW
Read more American Airlines reviews

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.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Gainesville (GNV)