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Flight Deals
Cheap Flights from Greenville to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Greenville 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 Greenville 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 Greenville to Caribbean
Fri, Dec 4 - Wed, Dec 16
8:52 pm - 8:37 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
22h 45m2 stops Tampa Fort Lauderdale
6:25 am - 7:53 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
26h 28m1 stop Fort Lauderdale
$233Multiple Airlines
Fri, Dec 4 - Thu, Dec 17
8:52 pm - 8:37 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
22h 45m2 stops Tampa Fort Lauderdale
5:35 pm - 8:13 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
15h 38m1 stop Fort Lauderdale
$244Multiple Airlines
Fri, Dec 4 - Sun, Dec 13
8:52 pm - 8:37 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
22h 45m2 stops Tampa Fort Lauderdale
6:25 am - 8:13 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
26h 48m1 stop Fort Lauderdale
$246Multiple Airlines
Thu, Dec 3 - Wed, Dec 9
2:50 pm - 12:50 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
9h 00m2 stops Baltimore/Washington Orlando
12:30 pm - 8:50 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
9h 20m2 stops Orlando Nashville Intl
$446Southwest
Wed, Feb 3 - Tue, Feb 9
1:05 pm - 12:35 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
10h 30m2 stops Baltimore/Washington Orlando
8:10 am - 6:15 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
11h 05m2 stops Orlando Nashville Intl
$448Southwest
Sun, Dec 6 - Fri, Dec 11
1:00 pm - 1:00 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
11h 00m2 stops Baltimore/Washington Orlando
11:20 am - 9:45 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
11h 25m2 stops Orlando Baltimore/Washington
$456Southwest
Mon, Jan 11 - Wed, Jan 20
8:04 pm - 12:28 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
15h 24m1 stop Miami
6:20 am - 11:27 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
6h 07m1 stop Charlotte Douglas
$466American Airlines
Tue, Jan 26 - Tue, Feb 2
10:47 am - 9:30 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
9h 43m2 stops Charlotte Douglas Miami
5:15 am - 1:14 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
8h 59m2 stops Miami Charlotte Douglas
$466American Airlines
Tue, Feb 2 - Tue, Feb 9
3:10 pm - 11:58 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
7h 48m1 stop Atlanta Hartsfield-Jackson
6:30 am - 2:22 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
8h 52m1 stop Atlanta Hartsfield-Jackson
$466Delta
Wed, Feb 3 - Tue, Feb 9
3:10 pm - 11:58 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
7h 48m1 stop Atlanta Hartsfield-Jackson
1:59 pm - 6:46 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
5h 47m1 stop Atlanta Hartsfield-Jackson
$466Delta
Recent one-way flight deals from Greenville to Caribbean
Fri, Dec 4
8:52 pm - 8:37 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
22h 45m2 stops Tampa Fort Lauderdale
$119Multiple Airlines
Mon, Nov 16
8:52 pm - 3:19 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
17h 27m2 stops Tampa Fort Lauderdale
$124Multiple Airlines
Fri, Nov 13
8:52 pm - 10:54 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
25h 02m2 stops Tampa Fort Lauderdale
$124Multiple Airlines
Tue, Nov 17
2:50 pm - 11:25 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
7h 35m1 stop Baltimore/Washington
$218Southwest
Tue, Nov 17
5:40 am - 12:42 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
6h 02m1 stop Atlanta Hartsfield-Jackson
$268Delta
Sun, Feb 21
7:30 am - 2:10 pmGSP Greenville-MBJ Montego Bay Sangster Intl
6h 40m1 stop Baltimore/Washington
$271Southwest
Thu, Nov 26
8:15 am - 6:40 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
9h 25m1 stop Baltimore/Washington
$285Southwest
Tue, Dec 29
6:00 am - 2:27 pmGSP Greenville-NAS Nassau Intl
8h 27m1 stop New York LaGuardia
$298Delta
Sat, Feb 13
8:28 pm - 10:16 amGSP Greenville-MBJ Montego Bay Sangster Intl
13h 48m1 stop Charlotte Douglas
$319American Airlines
Sat, Feb 13
8:28 pm - 10:20 amGSP Greenville-MBJ Montego Bay Sangster Intl
13h 52m2 stops Charlotte Douglas Miami
$319American Airlines
Recent last minute flight deals from Greenville to Caribbean
Thu, Nov 5 - Thu, Nov 12
10:12 am - 12:59 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
13h 47m2 stops Tampa Atlanta Hartsfield-Jackson
7:00 am - 8:51 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
26h 51m1 stop Fort Lauderdale
$325Multiple Airlines
Thu, Nov 5 - Sun, Nov 8
10:12 am - 12:59 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
37h 47m2 stops Tampa Atlanta Hartsfield-Jackson
7:00 am - 8:13 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
26h 13m1 stop Fort Lauderdale
$373Multiple Airlines
Thu, Nov 5 - Thu, Nov 12
4:02 pm - 10:15 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
17h 13m1 stop Orlando
7:00 am - 8:51 amSJU San Juan Luis Munoz Marin Intl-GSP Greenville
26h 51m1 stop Fort Lauderdale
$396Multiple Airlines
Sat, Oct 31 - Tue, Nov 3
5:25 pm - 10:45 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
17h 20m2 stops Dallas/Fort Worth Miami
11:35 am - 6:55 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
8h 20m2 stops Miami Charlotte Douglas
$608American Airlines
Thu, Nov 5 - Thu, Nov 12
1:00 pm - 1:00 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
11h 00m2 stops Baltimore/Washington Orlando
4:00 pm - 11:00 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
8h 00m2 stops Orlando Nashville Intl
$628Southwest
Mon, Nov 2 - Tue, Nov 3
1:00 pm - 12:55 amGSP Greenville-SJU San Juan Luis Munoz Marin Intl
10h 55m2 stops Baltimore/Washington Orlando
10:45 am - 6:10 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
8h 25m2 stops Orlando Nashville Intl
$643Southwest
Sat, Oct 31 - Tue, Nov 3
4:08 pm - 2:19 pmGSP Greenville-SJU San Juan Luis Munoz Marin Intl
22h 11m1 stop Miami
6:28 am - 4:27 pmSJU San Juan Luis Munoz Marin Intl-GSP Greenville
10h 59m1 stop Dallas/Fort Worth
$673American Airlines
Sat, Oct 31 - Sun, Nov 8
6:00 am - 1:32 pmGSP Greenville-SDQ Santo Domingo Las Americas
7h 32m1 stop Atlanta Hartsfield-Jackson
3:57 pm - 9:47 pmSDQ Santo Domingo Las Americas-GSP Greenville
6h 50m1 stop Atlanta Hartsfield-Jackson
$892Delta
Sat, Oct 31 - Sun, Nov 8
12:35 pm - 10:09 amGSP Greenville-SDQ Santo Domingo Las Americas
21h 34m2 stops Washington, D.C. Reagan-National Miami
2:55 pm - 10:17 amSDQ Santo Domingo Las Americas-GSP Greenville
20h 22m1 stop Philadelphia
$892American Airlines
Sat, Oct 31 - Sun, Nov 8
6:00 am - 6:06 pmGSP Greenville-SDQ Santo Domingo Las Americas
12h 06m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
3:57 pm - 9:47 pmSDQ Santo Domingo Las Americas-GSP Greenville
6h 50m1 stop Atlanta Hartsfield-Jackson
$897Delta
Booking Insights
KAYAK's insights & trends for Greenville to Caribbean flights
Get data-powered insights and trends into flights from Greenville to Caribbean to help you find the cheapest flights, the best time to fly and much more.
Prices
Airlines
More
Good to know
Low season | September |
|---|---|
High season | January |
Cheapest flight | $119 |
FAQs - booking Caribbean flights
Reviews of the top 3 airlines serving from Greenville to Caribbean
7.9
SouthwestOverall score based on 4225 reviews
7.0Food
8.1Boarding
7.4Entertainment
8.6Crew
8.0Comfort
Airline reviews
Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.
8.0 ExcellentLinda, Oct 2026
Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.
Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend
Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.
On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.
Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.
I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.
Friendly crew. Snacks were carb-heavy. Flight was quite delaye
Very good. Exactly what I expected. We did have a slight delay.
I think Southwest can offer a whole can of beverage instead of such a small cup
I like the boarding procedure. Handle the bird strike issue well.
Be on time. No issues with weather etc. entirely on airline.
Two of the flight attendants were cranky and seemed like they didn’t want to be there. Not up to normal Delta standards. And our bags didn’t make flight to Italy from Amsterdam resulting in having to make a trip back to airport which cost me 75 euros.
Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.
This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.
I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.
They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.
The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.
I just can’t understand why are you sell to many tickets ???? We had to wait 2 hours before 13 people from our flight take money and go to next day flight!
The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.
The plane was frigid, and leaked water from the ceiling all over me and my seat.
I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American
The first flight was delayed by an hour and a half, so we missed the second flight. They rebooked us on the later flight and I have to sit in the middle for more than 5 hours. Terrible experience. No more American Airlines.
Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!
Flight was fine, but not having WiFi was a major negative
Everything was excellent and I enjoyed myself. Thank for everything
One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service
I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization
Would have thought that they would gas up plane before everyone got on board
The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines
When my flight was delayed due to weather, I was rebooked to another flight since it showed that I would miss my connection. It was a lot of work to get back onto my originally connecting flight which was also delayed. That part caused a lot of stress and frustration. The ticketing agent at the desk was not very helpful.
More options for your flight to Caribbean
Complete your trip to Caribbean with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Greenville
Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Greenville
Flights from all regions of Greenville to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to popular destinations in Caribbean
Flights to Arubafrom $624
Flights to Cayman Islandsfrom $624
Flights to Cubafrom $2,556
Flights to Curaçaofrom $823
Flights to Dominican Republicfrom $654
Flights to Grenadafrom $737
Flights to Jamaicafrom $593
Flights to Puerto Ricofrom $267
Flights to Saint Kitts and Nevisfrom $821
Flights to St. Maartenfrom $657
Flights to The Bahamasfrom $419
Flights to Trinidad and Tobagofrom $719
Flights to Turks and Caicos Islandsfrom $552
Flights to U.S. Virgin Islandsfrom $638