$157 Find Cheap Flights from Greenville 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 Greenville to Caribbean departing on 9/5. 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 Greenville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$383
Santo Domingo
Santo Domingo1 stop$464
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$537
Nassau
Nassau1 stop$464
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$619
Port of Spain
Port of Spain1 stop$580
George Town
George Town1 stop$650
Willemstad
Willemstad2 stops$745
Aguadilla
Aguadilla3 stops$809
St. John's
St. John's2 stops$774
Punta Cana
Punta Cana1 stop$383
Santo Domingo
Santo Domingo1 stop$464
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$537
Nassau
Nassau1 stop$464
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$619
Port of Spain
Port of Spain1 stop$580
George Town
George Town1 stop$650
Willemstad
Willemstad2 stops$745
Aguadilla
Aguadilla3 stops$809
St. John's
St. John's2 stops$774

Book 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, Sep 11 - Tue, Sep 15
Delta Logo
5:45 am - 11:48 am
GSP
-
SJU
6h 03m
1 stop
Delta Logo
7:30 am - 2:52 pm
SJU
-
GSP
7h 22m
1 stop
$314Delta
Mon, May 18 - Sun, May 31
Multiple Airlines Logo
8:28 pm - 3:59 pm
GSP
-
SJU
43h 31m
2 stops
Multiple Airlines Logo
8:04 pm - 4:15 pm
SJU
-
GSP
20h 11m
1 stop
$318Multiple Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
6:00 am - 2:51 pm
GSP
-
SJU
8h 51m
1 stop
American Airlines Logo
6:00 am - 6:10 pm
SJU
-
GSP
12h 10m
1 stop
$319American Airlines
Fri, Jun 12 - Tue, Jun 16
Multiple Airlines Logo
10:26 am - 12:37 am
GSP
-
SJU
14h 11m
1 stop
Multiple Airlines Logo
5:15 pm - 2:58 pm
SJU
-
GSP
21h 43m
2 stops
$327Multiple Airlines
Fri, May 15 - Sun, May 31
Multiple Airlines Logo
5:43 pm - 3:50 pm
GSP
-
SJU
22h 07m
2 stops
Multiple Airlines Logo
8:04 pm - 4:15 pm
SJU
-
GSP
20h 11m
1 stop
$328Multiple Airlines
Mon, May 18 - Sun, May 31
Multiple Airlines Logo
8:28 pm - 10:18 am
GSP
-
SJU
13h 50m
1 stop
Multiple Airlines Logo
8:04 pm - 4:15 pm
SJU
-
GSP
20h 11m
1 stop
$330Multiple Airlines
Wed, May 13 - Tue, May 19
United Airlines Logo
2:52 pm - 9:24 pm
GSP
-
SJU
6h 32m
1 stop
United Airlines Logo
1:00 am - 11:14 am
SJU
-
GSP
10h 14m
1 stop
$336United Airlines
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
8:10 am - 11:59 pm
GSP
-
SJU
15h 49m
1 stop
American Airlines Logo
3:47 pm - 8:06 am
SJU
-
GSP
16h 19m
1 stop
$344American Airlines
Mon, Aug 17 - Tue, Aug 25
Delta Logo
6:45 am - 3:34 pm
GSP
-
MBJ
9h 49m
1 stop
Delta Logo
4:59 pm - 11:38 pm
MBJ
-
GSP
5h 39m
1 stop
$352Delta
Thu, Jul 2 - Fri, Jul 17
Breeze Airways Logo
3:40 pm - 8:55 am
GSP
-
NAS
17h 15m
1 stop
Breeze Airways Logo
9:55 am - 7:33 pm
NAS
-
GSP
9h 38m
1 stop
$471Breeze Airways
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.

What is the cheapest month to fly from Greenville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Greenville 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 Greenville to Caribbean is October, when tickets cost $431 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $736 and $625 respectively.

How far in advance should I book a flight from Greenville to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Greenville to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Greenville to Caribbean, you should book around 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$157
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Greenville to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Greenville 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 Greenville to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Greenville 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 Greenville 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 Greenville 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 Greenville 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 Greenville 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 3 airlines serving from Greenville to Caribbean

 
Need help choosing which airline to fly with from Greenville 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.
8.0
SouthwestOverall score based on 4334 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

2.0 MediocreGlenn, Apr 2026
SJC - PHX
Read more Southwest reviews

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

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.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

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.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports