$363 Find Cheap Flights from Gulfport 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 Gulfport to Caribbean Islands departing on 1/5. 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

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 Gulfport 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 Gulfport to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Gulfport to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$593
Montego Bay
Montego Bay2 stops$729
Bridgetown
Bridgetown2 stops$1,454
Punta Cana
Punta Cana2 stops$593
Montego Bay
Montego Bay2 stops$729
Bridgetown
Bridgetown2 stops$1,454

Book Cheap Gulfport 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 Gulfport 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 Gulfport to Caribbean Islands

Sun, Mar 1 - Thu, Mar 5
Delta Logo
2:54 pm - 11:58 pm
GPT
-
SJU
7h 04m1 stop
Delta Logo
3:55 pm - 9:54 pm
SJU
-
GPT
7h 59m1 stop
$365Delta
Sun, Feb 1 - Thu, Feb 12
American Airlines Logo
5:29 pm - 12:30 pm
GPT
-
SJU
17h 01m2 stops
American Airlines Logo
8:30 am - 4:05 pm
SJU
-
GPT
9h 35m1 stop
$405American Airlines
Sun, Mar 1 - Thu, Mar 5
American Airlines Logo
5:26 pm - 10:07 am
GPT
-
SJU
14h 41m2 stops
American Airlines Logo
7:30 am - 10:57 pm
SJU
-
GPT
17h 27m1 stop
$413American Airlines
Sun, Jan 25 - Thu, Jan 29
United Airlines Logo
7:00 am - 4:36 pm
GPT
-
SJU
7h 36m1 stop
United Airlines Logo
7:45 am - 3:58 pm
SJU
-
GPT
10h 13m1 stop
$485United Airlines
Sun, Jan 25 - Wed, Jan 28
United Airlines Logo
7:00 am - 4:36 pm
GPT
-
SJU
7h 36m1 stop
United Airlines Logo
2:05 am - 3:58 pm
SJU
-
GPT
15h 53m2 stops
$490United Airlines
Mon, Jan 26 - Thu, Jan 29
Air Canada Logo
1:57 pm - 12:25 pm
GPT
-
GCM
21h 28m2 stops
Air Canada Logo
1:30 pm - 3:58 pm
GCM
-
GPT
27h 28m2 stops
$1,110Air Canada
Mon, Jan 26 - Thu, Jan 29
Air Canada Logo
7:00 am - 12:25 pm
GPT
-
GCM
28h 25m2 stops
Air Canada Logo
1:30 pm - 3:58 pm
GCM
-
GPT
27h 28m2 stops
$1,145Air Canada
Thu, Dec 25 - Fri, Jan 2
Delta Logo
6:00 am - 3:05 pm
GPT
-
STT
7h 05m1 stop
Delta Logo
3:06 pm - 9:40 pm
STT
-
GPT
8h 34m1 stop
$1,783Delta
Sat, Feb 14 - Wed, Feb 18
WestJet Logo
10:25 am - 3:23 pm
GPT
-
ANU
26h 58m2 stops
WestJet Logo
4:20 pm - 9:54 pm
ANU
-
GPT
31h 34m2 stops
$4,008WestJet
Sat, Feb 14 - Wed, Feb 18
WestJet Logo
10:25 am - 3:23 pm
GPT
-
ANU
26h 58m2 stops
WestJet Logo
4:20 pm - 9:54 pm
ANU
-
GPT
31h 34m2 stops
$4,015WestJet
Booking Insights

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

Get data-powered insights and trends into flights from Gulfport 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 Gulfport 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 $387, prices are generally cheapest when you fly direct.

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

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

For Gulfport to Caribbean Islands, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Gulfport, the best deals are generally found on Tuesday, with Thursday being the most expensive.

Good to know

Low seasonDecember
Cheapest flight$148
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Gulfport to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Gulfport 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 Gulfport 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 Gulfport 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 Gulfport 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 Gulfport 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 in the afternoon, when round-trip flights cost $380 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 $589.

Reviews of the top airlines flying from Gulfport to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Gulfport 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 Gulfport 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.
7.9
DeltaOverall score based on 8008 reviews
7.3Food
8.5Crew
7.9Entertainment
7.9Comfort
8.1Boarding
Airline reviews

None of the airplane features were available during the flight.

4.0 OkayAnonymous, Dec 2025
JFK - SDQ
Read more Delta reviews

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports