$208 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 7/24. 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 Cana1 stop$505
Montego Bay
Montego Bay2 stops$372
Bridgetown
Bridgetown2 stops$2,405
Punta Cana
Punta Cana1 stop$505
Montego Bay
Montego Bay2 stops$372
Bridgetown
Bridgetown2 stops$2,405

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

Mon, Mar 2 - Thu, Mar 5
Multiple Airlines Logo
6:54 pm - 2:25 am
GPT
-
SJU
5h 31m
1 stop
Multiple Airlines Logo
2:00 am - 9:00 am
SJU
-
GPT
9h 00m
1 stop
$315Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
6:54 pm - 2:25 am
GPT
-
SJU
5h 31m
1 stop
Multiple Airlines Logo
10:12 pm - 5:40 pm
SJU
-
GPT
45h 28m
2 stops
$346Multiple Airlines
Fri, Jun 12 - Fri, Jun 26
American Airlines Logo
7:53 pm - 1:32 pm
GPT
-
MBJ
17h 39m
2 stops
American Airlines Logo
12:30 pm - 10:48 am
MBJ
-
GPT
22h 18m
2 stops
$372American Airlines
Wed, Apr 22 - Wed, Apr 29
Delta Logo
2:40 pm - 11:12 pm
GPT
-
SJU
7h 32m
1 stop
Delta Logo
7:30 am - 1:54 pm
SJU
-
GPT
7h 24m
1 stop
$376Delta
Thu, Apr 23 - Thu, Apr 30
American Airlines Logo
6:10 pm - 10:48 am
GPT
-
SJU
15h 38m
1 stop
American Airlines Logo
7:25 am - 11:58 pm
SJU
-
GPT
17h 33m
1 stop
$396American Airlines
Thu, Apr 2 - Thu, Apr 9
United Airlines Logo
7:10 am - 12:30 pm
GPT
-
GCM
5h 20m
1 stop
United Airlines Logo
1:35 pm - 7:53 pm
GCM
-
GPT
6h 18m
1 stop
$627United Airlines
Mon, May 4 - Thu, May 7
United Airlines Logo
7:07 am - 1:30 pm
GPT
-
MBJ
6h 23m
1 stop
United Airlines Logo
4:12 pm - 7:53 pm
MBJ
-
GPT
27h 41m
2 stops
$672United Airlines
Thu, Mar 5 - Sat, Mar 21
Delta Logo
6:00 am - 12:53 pm
GPT
-
MBJ
5h 53m
1 stop
Delta Logo
4:49 pm - 8:50 am
MBJ
-
GPT
16h 01m
1 stop
$1,016Delta
Sun, Mar 1 - Thu, Mar 5
Air Canada Logo
7:05 am - 3:55 pm
GPT
-
BGI
30h 50m
2 stops
Air Canada Logo
4:10 pm - 7:45 pm
BGI
-
GPT
29h 35m
2 stops
$2,405Air Canada
Sun, Mar 1 - Thu, Mar 5
Air Canada Logo
7:05 am - 4:25 pm
GPT
-
UVF
31h 20m
2 stops
Air Canada Logo
5:15 pm - 7:45 pm
UVF
-
GPT
28h 30m
2 stops
$2,632Air Canada
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 $417, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$208
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 1% 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.

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 8207 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

2.0 MediocreDimitrios, Feb 2026
JFK - DFW
Read more Delta reviews

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports