$268 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 3/30. 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$1,273
Montego Bay
Montego Bay1 stop$484
Nassau
Nassau1 stop$566
Kingston
Kingston2 stops$690
Simpson Bay
Simpson Bay1 stop$642
St. John's
St. John's1 stop$671
Punta Cana
Punta Cana1 stop$1,273
Montego Bay
Montego Bay1 stop$484
Nassau
Nassau1 stop$566
Kingston
Kingston2 stops$690
Simpson Bay
Simpson Bay1 stop$642
St. John's
St. John's1 stop$671

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

Wed, Apr 15 - Sat, Apr 18
American Airlines Logo
7:59 pm - 10:53 am
GNV
-
SJU
14h 54m
2 stops
American Airlines Logo
1:31 pm - 11:59 pm
SJU
-
GNV
10h 28m
1 stop
$431American Airlines
Mon, Jul 13 - Thu, Jul 16
American Airlines Logo
9:48 am - 10:59 pm
GNV
-
SJU
13h 11m
1 stop
American Airlines Logo
7:14 pm - 11:59 pm
SJU
-
GNV
4h 45m
1 stop
$436American Airlines
Sat, May 9 - Sat, May 16
American Airlines Logo
7:59 pm - 10:53 am
GNV
-
SJU
14h 54m
2 stops
American Airlines Logo
7:25 am - 7:33 pm
SJU
-
GNV
12h 08m
1 stop
$471American Airlines
Tue, Jun 30 - Wed, Jul 8
Delta Logo
6:33 am - 1:31 pm
GNV
-
SJU
6h 58m
1 stop
Delta Logo
6:00 am - 12:23 pm
SJU
-
GNV
6h 23m
1 stop
$476Delta
Sun, May 17 - Sun, May 24
American Airlines Logo
7:59 pm - 10:53 am
GNV
-
SJU
14h 54m
2 stops
American Airlines Logo
10:29 am - 11:59 pm
SJU
-
GNV
13h 30m
1 stop
$481American Airlines
Thu, Apr 2 - Sat, Apr 4
Delta Logo
6:00 am - 1:54 pm
GNV
-
SXM
7h 54m
1 stop
Delta Logo
4:33 pm - 9:29 am
SXM
-
GNV
16h 56m
1 stop
$927Delta
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:00 am - 7:15 pm
GNV
-
STI
13h 15m
2 stops
Delta Logo
6:00 am - 10:39 pm
STI
-
GNV
16h 39m
2 stops
$1,051Delta
Tue, Aug 18 - Sun, Aug 23
WestJet Logo
7:05 pm - 11:45 am
GNV
-
MBJ
17h 40m
2 stops
WestJet Logo
7:30 pm - 6:24 pm
MBJ
-
GNV
21h 54m
2 stops
$1,637WestJet
Tue, Aug 25 - Fri, Aug 28
WestJet Logo
6:00 am - 11:10 am
GNV
-
NAS
29h 10m
2 stops
WestJet Logo
12:00 pm - 10:30 pm
NAS
-
GNV
34h 30m
2 stops
$1,679WestJet
Fri, Jul 10 - Tue, Jul 14
WestJet Logo
7:01 pm - 6:30 pm
GNV
-
MBJ
24h 29m
2 stops
WestJet Logo
12:45 pm - 12:23 pm
MBJ
-
GNV
22h 38m
2 stops
$1,706WestJet
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 ($431) and Delta ($1,051).

Good to know

Low seasonFebruary
Cheapest flight$227
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Gainesville to Montego Bay

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 11488 reviews
6.9Entertainment
7.9Crew
7.2Comfort
7.5Boarding
6.4Food
Airline reviews

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

8.0 ExcellentAnonymous, Mar 2026
MIA - LIM
Read more American Airlines reviews

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports