$238 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 8/19. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Caribbean Islands Flight Deals from Gainesville

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$517
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$476
Kingston
Kingston1 stop$619
Simpson Bay
Simpson Bay2 stops$632
Bridgetown
Bridgetown1 stop$683
Punta Cana
Punta Cana2 stops$517
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$476
Kingston
Kingston1 stop$619
Simpson Bay
Simpson Bay2 stops$632
Bridgetown
Bridgetown1 stop$683

Cheap Flights from Gainesville to Caribbean Islands

 
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

Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
8:12 pm - 12:05 pmGNV-SJU
14h 53m2 stops
American Airlines Logo
12:50 pm - 10:18 pmSJU-GNV
10h 28m1 stop
$365American Airlines
Find Deal
Sat, Dec 27 - Tue, Jan 13
American Airlines Logo
8:07 pm - 1:30 pmGNV-SJU
16h 23m1 stop
American Airlines Logo
9:20 am - 12:08 amSJU-GNV
15h 48m2 stops
$455American Airlines
Find Deal
Wed, Nov 19 - Sat, Nov 22
American Airlines Logo
6:42 am - 5:15 pmGNV-SJU
9h 33m2 stops
American Airlines Logo
4:55 pm - 11:50 pmSJU-GNV
7h 55m1 stop
$470American Airlines
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
6:45 pm - 12:40 pmGNV-AUA
17h 55m2 stops
Delta Logo
1:55 pm - 9:25 amAUA-GNV
19h 30m2 stops
$474Delta
Find Deal
Tue, Oct 21 - Tue, Oct 28
American Airlines Logo
6:00 am - 12:30 pmGNV-PLS
6h 30m1 stop
American Airlines Logo
1:20 pm - 11:50 pmPLS-GNV
10h 30m1 stop
$474American Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:00 am - 11:48 amGNV-NAS
5h 48m1 stop
Delta Logo
3:14 pm - 10:41 pmNAS-GNV
7h 27m1 stop
$476Delta
Find Deal
Tue, Oct 21 - Tue, Oct 28
American Airlines Logo
6:00 am - 12:30 pmGNV-PLS
6h 30m1 stop
American Airlines Logo
11:25 am - 10:09 amPLS-GNV
22h 44m2 stops
$478American Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
American Airlines Logo
4:43 pm - 9:45 amGNV-NAS
17h 02m2 stops
American Airlines Logo
2:50 pm - 8:50 amNAS-GNV
18h 00m2 stops
$485American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
10:15 am - 12:32 pmGNV-PUJ
26h 17m2 stops
Delta Logo
1:53 pm - 5:34 pmPUJ-GNV
27h 41m2 stops
$517Delta
Find Deal
Sat, Oct 11 - Wed, Oct 15
WestJet Logo
6:35 pm - 1:43 pmGNV-MBJ
44h 08m2 stops
WestJet Logo
10:30 am - 10:27 pmMBJ-GNV
10h 57m2 stops
$1,697WestJet
Find Deal
Useful Info

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 $496, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gainesville to Caribbean Islands, 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 Islands is November, when tickets cost $351 (return) on average. On the other hand, the most expensive months are September and December, when the average cost of round-trip tickets is $1,007 and $780 respectively.

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.


Good to know

Low seasonOctober
High seasonMay
Cheapest flight$238
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Gainesville to San Juan

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 10000 reviews
7.2Comfort
8.0Crew
6.5Food
7.5Boarding
6.9Entertainment
Airline reviews

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

4.0 OkayAnonymous, Jun 2025MIA - GIG
Read more American Airlines reviews

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.